The Bing Crosby Albums Ranked

Approaching the entire discography of Old Hollywood superstar Bing Crosby as a listener is a daunting task, let alone as someone attempting to write about the man. Crosby, by many accounts a more than difficult person and also one of the most popular and enduring musical artists of all time, began recording in 1927 as a member of Paul Whiteman’s orchestra. Fifty years later, in 1977, the final album completed within his lifetime was released. Crosby’s career straddled many tumultuous changes in show business and the world at large, but its ending in the very year of disco’s explosion, after its beginning in the jazz-fueled Roaring ’20s, is especially remarkable to me.

Now, I mentioned the difficulty in comprehensively approaching Crosby’s albums as a writer, especially since I like to qualify how I come at these ranked articles. First of all, the “album” concept as we know it wasn’t in practice at the beginning of the singer’s career. Even 12 years in, when his first compilation record was released in 1939, the concept of an album was that it brought together a bunch of previously released singles, perhaps those from several years earlier. But the Bing Crosby album “originality,” you might call it, was distinguished early by film soundtrack records. These brand-new releases of course followed a cohesive theme, as a modern album often does to some extent. And eventually, Crosby like everyone else would conform to our modern expectations in the “album era” that really took root in the mid-to-late 1950s.

So this being said, I’ve taken some different steps in ranking Crosby’s discography. First, I usually omit compilation albums, but since they make up much of the record releases for Crosby in the first decades of his career, I’ve included those. However, I did leave out later compilations that retread ground already covered by those early collections, especially posthumous ones. Second, what constitutes a “Bing Crosby album” in terms of length is pretty variable. I usually acknowledge but don’t rank EPs since they are kind of miniature releases compared to “full-fledged” original albums; it’s somewhat unfair to put them side by side sometimes. In the case of Crosby, though, a lot of his early albums would be considered abbreviated by today’s standards, even if they pushed the limits of the time, and I didn’t want to rule them out for that reason. Third, that “Bing Crosby album” moniker I broadly interpreted to include movie cast albums and collaborations, of which he was usually top-billed anyways, minus a few “various artists” collections on which he appeared in the distinct minority of tracks. Fourth and finally, I usually skip past Christmas or holiday albums since I often regard them as separate entities not really relevant to an artist’s discography…and I often don’t really like them besides. But we’re talking about the performer of “White Christmas,” so it would be pretty wild to ignore a huge swath of Crosby’s discography for which he is also best known. What I did float by, however, was the sizable number of children’s tale narration albums Crosby did over the years.

Now all this being said, there are quite a few releases that I could have possibly counted but I wasn’t able to track them down or I simply wasn’t aware of them. There are many, many records credited to Bing Crosby out there. But my little “canon” I’ve created here constitutes a whopping 102 albums, which still certainly omits chunks of original material here and there, released in the 38 years from 1939 to 1977. I’ll “only” write up the top 50 here, while providing the rest of the ranking in pure list form at the bottom of this piece. Whew. If you made it this far, I hope you like cheesy, old, croon-y, creaky, sometimes problematic pop music.

#50 — THAT TRAVELIN’ TWO-BEAT (1965)

Favorite track: “That Travelin’ Two-Beat”

We essentially start this list with the middling Bing Crosby albums, not his worst. THAT TRAVELIN’ TWO-BEAT, a collaboration with WHITE CHRISTMAS (1954) co-star Rosemary Clooney, followed the nadir of Crosby’s career in the early 1960s and a late ’50s “around the world” concept record with Clooney. THAT TRAVELIN’ TWO-BEAT is certainly worse than that album (FANCY MEETING YOU HERE) as it applies a Dixieland two-beat arrangement to the “global” songs. Often, it plays cheaply, even though Billy May did the arranging. Still, THAT TRAVELIN’ TWO-BEAT is a lively and enjoyable journey with a career highlight partner in Clooney.

#49 — A CHRISTMAS SING WITH BING AROUND THE WORLD (1956)

Favorite track: “White Christmas”

I might as well get my approach to Christmas albums out of the way already. On the whole, I can’t bring myself to suffer through them in many modern artists’ discographies. But I don’t want to sound like a scrooge; indeed, I like a lot of Christmas music. It just has to be old for the most part, I must admit. The particular cheesiness of Christmas music is best channeled through the corniness of old pop and jazz, as well as the ethereal sonic qualities those eras were able to achieve. So besides including them on the list period, many of the Crosby Christmas albums weren’t just tolerated, but actively enjoyed by me. A CHRISTMAS SING WITH BING AROUND THE WORLD is nevertheless a minor work in the singer’s signature subgenre. Sourced from a radio broadcast that saw Crosby introducing choirs from, well, around the world, A CHRISTMAS SING also showcases his pipes on a number of tunes. First and foremost is “White Christmas,” Crosby’s and the whole music industry’s biggest hit (it’s still the best-selling single of all time I believe), but in a more low-key approach; it wasn’t just a re-broadcast of the old recording. The concept of A CHRISTMAS SING, which calls to mind something like the “It’s a Small World” Disneyland ride, is a little old-fashioned and often plays as naive, but the collective experience is warm.

#48–12 SONGS OF CHRISTMAS (1964)

Favorite track: “White Christmas”

One of a couple collaborations with Frank Sinatra and Fred Waring, 12 SONGS OF CHRISTMAS is pretty rote. But after hearing Michael Bublé or Harry Connick Jr. or whoever in that vein for the past season, it’s positively refreshing to hear the old paradigm of Christmas music. 12 SONGS OF CHRISTMAS isn’t very exciting, and indeed the standout track, another adaptation of “White Christmas,” doesn’t even feature Crosby or Sinatra. But Waring’s Pennsylvanians choir does the song justice in a peaceful way before opening up a downtempo experience for the rest of the album. Part of 12 SONGS OF CHRISTMAS’ appeal, I think, also stems from its arrival in the midst of a particularly dire time in Crosby’s career and its ability to play at the very least as a revisiting of his good stuff.

#47 — A TIME TO BE JOLLY (1971)

Favorite track: “I Sing Noel”

This late-era Crosby album was actually his last in the Christmas mold. There’s no “White Christmas” or any of the other standards he popularized or memorably interpreted over the years on A TIME TO BE JOLLY, which is essentially its appeal. And although Crosby for decades had been criticized to different extents for his worn-down voice, the old man’s pipes sound smooth, especially augmented by the record’s chorus and even over the chintzy instrumentation. A TIME TO BE JOLLY gets a little groovy, as on standout track “I Sing Noel,” marking the approach of Crosby’s ’70s and a slight evolution in the style of music with which he is most famously associated.

#46 — FEELS GOOD, FEELS RIGHT (1976)

Favorite track: “Time on My Hands”

As one of the final Crosby albums, FEELS GOOD, FEELS RIGHT carries the weary nostalgia that defined the singer’s last few years. For some, it may be unappealingly sentimental…but then, that could be said for the whole of Crosby’s career. But in fact, the album weaves a soft sound with impressive strings and a not over-powering drum sound (something that happened kind of a lot in the mixes of this era for Crosby). FEELS GOOD, FEELS RIGHT isn’t the highlight of Crosby’s final years, but it does showcase his ability to provide a distinct sense of wistfulness.

#45 — ROBIN AND THE 7 HOODS (1964)

Favorite track: “Style”

This was a difficult one to classify as a “Bing Crosby album.” ROBIN AND THE 7 HOODS, the soundtrack of the star-studded film of the same name, doesn’t always feature Crosby on its songs. But the collective talents of Sinatra, Dean Martin, Sammy Davis Jr., and even Peter Falk are represented nearly equally. And in the record’s standout track, “Style,” the Crosby-Sinatra-Martin trio deliver one of the greatest songs in their respective discographies. The rest of ROBIN AND THE 7 HOODS can be quite amusing as often as it plays more weakly without the visual component of the movie, but it’s ultimately a joyous and swinging listen.

#44 — I WISH YOU A MERRY CHRISTMAS (1962)

Favorite track: “Frosty the Snowman”

Crosby’s takes on many Christmas standards for I WISH YOU A MERRY CHRISTMAS don’t really rival their best prior renditions, including even my favorite cut “Frosty the Snowman.” But for the most part, it is able to deliver the Christmas spirit effectively enough. I WISH YOU A MERRY CHRISTMAS may sound diminished in comparison to “rivals” and Crosby’s own other holiday offerings, but it satisfies.

#43 — GOING MY WAY (1945)

Favorite track: “Swinging on a Star”

“Swinging on a Star” is probably one of Crosby’s biggest songs and its source movie, GOING MY WAY (1944), is also one of the films for which he is best known. The soundtrack album following the year after the movie’s release may not live up to those standards, but it is on the whole a pleasant and at turns lively and soul-stirring experience. GOING MY WAY’s greatest significance is its exponent of its hit single, but the rest of its tracks aren’t bitter disappointments.

#42 — THE BELLS OF ST. MARY’S (1946)

Favorite track: “The Bells of St. Mary’s”

The follow up both as film and album to GOING MY WAY, THE BELLS OF ST. MARY’S (1945 movie) is also one of Crosby’s best-known works. More of an emotional drama than GOING MY WAY, THE BELLS OF ST. MARY’S album is correspondingly more croon-y, wistful, and sad. There is something about the orchestration of the album, a quality affected by the recording technology and contemporary styles, that makes it feel somewhat magical. But then that could be said for a lot of Crosby’s 1930s and ’40s work especially and I’ll say more about it soon enough, as for as good as it is, THE BELLS OF ST. MARY’S isn’t even the best example of this phenomenon.

#41 — ROAD TO UTOPIA (1946)

Favorite track: “Road to Morocco”

The “Road to…” film series Crosby made with Bob Hope is variably funny, always problematic. Many find Hope insufferable in any context, but even as someone who generally finds Hope pretty entertaining, the music that came out of those movies was middling by both artists’ standards. Although ostensibly a soundtrack for the film of the same name, ROAD TO UTOPIA also features the title track from ROAD TO MOROCCO (1942) of a few years earlier, and it’s the best one on the record. The rest of ROAD TO UTOPIA isn’t terrible and can in fact offer some upbeat entertainment, especially as it precedes the decline in quality for the rest of the Road to… albums.

#40 — BING CROSBY SINGS WITH AL JOLSON, BOB HOPE, DICK HAYMES AND THE ANDREWS SISTERS (1948)

Favorite track: “Road to Morocco”

Did someone say “Road to Morocco?” Although I noted in my introduction that I would skip by compilations with overlaps, I made exceptions where such overlaps were minor, as in the case of the ridiculously titled BING CROSBY SINGS WITH AL JOLSON, BOB HOPE, DICK HAYMES AND THE ANDREWS SISTERS. In the late ’40s and early ’50s, Crosby’s record label Decca was issuing a slew of releases capitalizing on their star’s success, mostly compiling singles they hadn’t already issued in album form. And a series within that slew grabbed a bunch of Crosby’s high-profile collaborations, which you can see represented in the very title of this BING CROSBY SINGS. As an assortment of co-credits and tonal differences, it’s hard to evaluate the collective experience of the album, but ultimately, the AL JOLSON, BOB HOPE, DICK HAYMES AND THE ANDREW SISTERS record brings enough solid tunes to the table to earn its place slightly above the mid-line of Crosby’s work.

#39 — COLLECTORS’ CLASSICS — VOL. 5 (1951)

Favorite track: “I Have Eyes”

Remember how I said Decca was just putting out a ton of Crosby compilations in the late ’40s and early ‘50s? Well, the eight volume COLLECTORS’ CLASSICS series was sort of the apotheosis of this strategy. Pulling together numerous songs from many Crosby films from as early as HERE IS MY HEART (1934) through the rest of the ’30s to ROAD TO SINGAPORE (1940), it must be said that these records mostly did issue, in album form, singles that had never appeared as such. Hence, my inclusion of COLLECTORS’ CLASSICS on this list. Ranking them, however, comes all the way down to which movies/songs were curated for each volume, which usually feature two films. VOL. 5 carries SING YOU SINNERS (1938) and PARIS HONEYMOON (1939), not necessarily the greatest exports of Crosby hits, but satisfying enough in that early Crosby mode so as to provide decent enjoyment.

#38 — THOROUGHLY MODERN BING (1968)

Favorite track: “Up, Up and Away”

THOROUGHLY MODERN BING is so, so close to being unbearably cheesy. For many, it probably is. But for me, there’s something to its jangly instrumentation and approximation of some mid 1960s pop sounds that is thoroughly endearing. Crosby’s voice was in a kind of awkward stage where he wasn’t resting in his pocket of old man voice and still attempting to hit his younger range, but it never sounds as terrible as it could earlier in the decade with his string of singalong albums. THOROUGHLY MODERN BING is corny even by Crosby standards, and its arrangements aren’t lush like in his heyday, but it’s old-school counterprogramming to the crazy changes of the late ‘60s.

#37 — THAT’S WHAT LIFE IS ALL ABOUT (1975)

Favorite track: “That’s What Life Is All About”

The first of a few albums at the tail end of Crosby’s career and life resulting from a series of United Artists London recording sessions, THAT’S WHAT LIFE IS ALL ABOUT feels like the first major reckoning with the singer’s age and place in history. Its orchestration mostly operates in an airy mode, veering into restrained jollity here and there, to great effect. The title track soars into high emotion and an evocation of nostalgia. Some elements of the record, primarily its deviation from the cheaper sounds of Crosby’s ’60s, make it sound like an attempt to capture the old magic. Although it isn’t wholly successful in that way, THAT’S WHAT LIFE IS ALL ABOUT is relatively successful as a marker in the new yet final era for the aged crooner.

#36 — HIGH SOCIETY (1956)

Favorite track: “High Society Calypso”

HIGH SOCIETY was the soundtrack for the film of the same name starring Crosby, Sinatra, Grace Kelly, and Louis Armstrong. Armstrong’s presence on the album is relatively limited, but his presence is so strong that the record’s standout track, “High Society Calypso,” doesn’t even feature Crosby. Fittingly, it’s a lively calypso-esque track that does exist in a world apart from the rest of the songs that follow it. But those songs that do follow are fun in their own way, hitting jazz notes that Crosby didn’t always dip into, making HIGH SOCIETY a more significant album in his vast discography.

#35 — SEASONS (1977)

Favorite track: “Seasons”

SEASONS was the last album Bing Crosby completed within his lifetime, although it was released shortly after his death in 1977. Its central concept, charting the changes of a year, is a fitting sendoff for a performer who had worked in so many eras. It’s difficult to not assign more weight to such a release, but even still, SEASONS continues Crosby’s final “London” sound of light yet stirring strings paired with ruminative lyrics. The final moments of its title track sound as good as most anything Crosby did before, and while the songs that follow don’t match this intensity, they stay within a pocket of nostalgia and dreaminess. SEASONS is an imperfect conclusion to the Crosby saga, but a significantly affecting one nevertheless.

#34 — COLLECTORS’ CLASSICS — VOL. 2 (1951)

Favorite track: “Without a Word of Warning”

Grabbing tunes from TWO FOR TONIGHT (1935) and the earlier film version of ANYTHING GOES (1936), COLLECTORS’ CLASSICS — VOL. 2 is solid. It vibrates with that ’30s sound, which warbles somewhat when Crosby hits those louder and higher notes, and much of VOL. 2’s songs have the occasion to showcase that in a pleasing manner.

#33 — COLLECTORS’ CLASSICS — VOL. 3 (1951)

Favorite track: “Empty Saddles”

A slight improvement over VOL. 2, COLLECTORS’ CLASSICS VOL. 3 moves the timeline forward just a bit to cover RHYTHM ON THE RANGE (1936) and PENNIES FROM HEAVEN (1936), two of Crosby’s most iconic movies. And in spite of the presence of the great “Pennies from Heaven,” the proto-pop-country Crosby practiced for songs like “Empty Saddles” are so plaintive and beautiful in their own way. But combined, the movies represented on VOL. 3 make it one of the highlights of the COLLECTORS’ CLASSICS series, as well as the whole Crosby discography.

#32 — BING CROSBY SINGS SONGS BY GEORGE GERSHWIN (1949)

Favorite track: “I Got Plenty o’ Nuttin’”

Besides their trends of collaboration compilations and film retrospectives with the COLLECTORS’ CLASSICS albums, Decca also put out a couple of composer-themed records. BING CROSBY SINGS SONGS BY GEORGE GERSHWIN is one of the best of these, fitting since Gershwin was a pretty good songwriter. In spite of its 1949 release, most of the record’s songs date back to the late ’30s, including standout “I Got Plenty o’ Nuttin’,” which means it has those same qualities I find appealing about the COLLECTORS’ CLASSICS volumes. SONGS BY GEORGE GERSHWIN features some of Gershwin’s most famous tunes, and even if Crosby’s renditions aren’t the best versions of them, they are significantly moving.

#31 — LE BING (1953)

Favorite track: “La Mer”

LE BING, in case you couldn’t tell from that evocative title, is an album of French songs. And in fact, Crosby recorded it in Paris and in the native tongue, not the first or last time foreign language tunes would receive that treatment from him. And on the whole, it’s a successful effort. Many of the songs are balladic, including my favorite “La Mer,” but when things get more upbeat it’s refreshing. Ultimately, the tone of LE BING is enrapturing, with bright backing and Crosby’s voice in good form in spite of the wearing down happening in the early ‘50s.

#30 — HOLIDAY IN EUROPE (1962)

Favorite track: “April in Portugal”

HOLIDAY IN EUROPE, as you may have been able to tell by now, was one of quite a few “around the world” albums Crosby made, solo or with Clooney. This album is a former effort and it might as well have been a bolt of beautiful lightning coming on the heels, as it did, of Crosby’s awful singalong albums of the early ’60s. His voice sounds, by comparison, strikingly powerful and sinuous, rather than reverbed and subsumed by cheap, karaoke-esque instrumentation. The liveliness of HOLIDAY IN EUROPE’s arrangements are as responsible for the album’s success as Crosby’s revived voice.

#29 — A SOUTHERN MEMOIR (1975)

Favorite track: “Alabamy Bound”

A SOUTHERN MEMOIR came after the biggest gap between Crosby albums in a monstrously prolific and long career, just about three whole years in fact. Only a few years earlier did he miss a calendar year or release “only” one record in a year and these slowdowns were only matched in the war years, when between 1942 and 1945 no new Crosby vinyl was produced (although he was still very active in film and radio). This ’70s slowdown, though, would of course be attributed not only to old age, but also tumors on his lungs that were removed in 1974. Somehow, Crosby was able to return to singing and not really in a diminished capacity compared to his late ‘60s/early ’70s work. His range was more reduced than ever, but in his approach to nostalgia and reflection, the lower register was fitting. In the case of A SOUTHERN MEMOIR, however, Crosby came out swinging with more lively tunes than what would follow it. I usually don’t love old-school “southern” themed things; just hits a little too close to Confederate worship for me. But A SOUTHERN MEMOIR’s appeal is not in its lyrical approach but in its relatively radical descent into upbeat jazz and funk music, especially on my favorite track “Alabamy Bound.”

#28 — WAY BACK HOME (1951)

Favorite track: “Way Back Home”

When Decca couldn’t find other collaborations, old movie soundtracks, or specific composers with which to group past Crosby hits together, they went for general concepts like “homesickness,” as in the case of WAY BACK HOME. But I suppose that was in good taste because the album, contrived as it is, waltzes with a wistfulness and quaintness that make it smooth backing to relaxation. WAY BACK HOME isn’t the most innovative Crosby release but it offers laid-back crooning in spades.

#27 — DON’T FENCE ME IN (1946)

Favorite track: “I’m Thinking Tonight of My Blue Eyes”

I’ve somehow gone this far without mentioning Crosby’s numerous collaborations with the Andrews Sisters. This trio of harmonious singers hit a certain sound that I haven’t quite heard replicated at the time or in any era. There’s an uncanny vibration the Andrews Sisters tap into that makes for really pleasing sounds that both place their music very much in the past but also out of time. This metaphysical musing is just to say that DON’T FENCE ME IN, a collection of country-western tunes, traded on the huge success of the Andrews Sisters-featuring “Pistol Packin’ Mama.” While the rest of the album sees Crosby go solo, I had to take the opportunity to address his frequent partners, and to address the fact that they open an album that’s more “tinged” with country than it is steeped in it. DON’T FENCE ME IN is good pop though.

#26 — JEROME KERN (1946)

Favorite track: “Till the Clouds Roll By”

This Crosby-sung collection of songs written by Jerome Kern just happens to hit a dreamy vein that consistently impresses me. The record doesn’t necessarily have traits that distinguish it on its face from many of the other kinds of Crosby albums I’ve already written about, but JEROME KERN is just one of those great collections from the singer’s heyday.

#25 — JUST FOR YOU (1952)

Favorite track: “Just for You”

Much of JUST FOR YOU’s success could be attributed to Jane Wyman, the album’s collaborator and Crosby’s costar in the film of the same name. Her swooning voice leads a couple of songs and accompanies Crosby’s on another, while the Andrews Sisters pop up to close the record as well. Together, these performers make JUST FOR YOU a surprisingly diverse experience, from the sensuous angst of the title track to Wyman’s heartfelt “Checkin’ My Heart” to the cheesily upbeat “The Live Oak Tree” with the Andrews Sisters.

#24 — BING CROSBY SINGS WITH JUDY GARLAND, MARY MARTIN, JOHNNY MERCER (1948)

Favorite track: “Lily of Laguna”

As another of those “partnership” collections Decca populated the field with, BING CROSBY SINGS WITH JUDY GARLAND, MARY MARTIN, JOHNNY MERCER succeeds in my book thanks to its preponderance of Garland collaborations. Ironically, my single favorite tune on the album, “Lily of Laguna,” is a duet with Mary Martin, but the point still stands. Besides the fully entertaining half with Garland, the rest of the JUDY GARLAND, MARY MARTIN, JOHNNY MERCER release is able to keep up the energy and make an impression in the vast sea of Crosby’s discography.

#23 — BING: A MUSICAL AUTOBIOGRAPHY (1954)

Favorite track: “Sweet Leilani”

Crosby thought he was going to retire in 1954, a humorous thing to consider in retrospect since he really didn’t have any lag time between releases and wouldn’t ultimately leave the singing scene until his death 23 years later. But in the meantime, he re-interpreted many of his biggest hits with BING: A MUSICAL AUTOBIOGRAPHY, a massive five-disc set that I can’t imagine wasn’t informed by frequent singing and dancing partner Fred Astaire’s 1952 album THE ASTAIRE STORY. Like that record, Crosby provides a bit of narration ahead of each redo, setting the scene for how things came about or how he feels about the songs now with a general warmth and a bit of humor. However, more than half of A MUSICAL AUTOBIOGRAPHY is actually a greatest hits of previously recorded songs, but what is evaluated here is Crosby’s newer versions made with the Buddy Cole Trio. They’re on the whole not as good as their predecessors, especially the originally heavenly “Sweet Leilani” turned pretty good adaptation, but the scope of A MUSICAL AUTOBIOGRAPHY is hard to deny, as is its ultimately impressive quality.

#22 — A COUPLE OF SONG AND DANCE MEN (1975)

Favorite track: “A Couple of Song and Dance Men”

Speaking of Astaire: Crosby and the iconic dancer’s final collaboration was a full-throated original album. Recorded near the end of their respective careers, A COUPLE OF SONG AND DANCE MEN also came out of the London sessions that produced Crosby’s last few records. Together, Crosby and Astaire tackle some of the songs for which they were already known, both separately and together. Crosby’s age wears a little more thin here than it does on his decidedly more downtempo releases of the time, but he hits an incredible note on the title track. And the duo’s banter is humorous and heartwarming considering the years between them. A COUPLE OF SONG AND DANCE MEN is fueled by two times the late career energy I find so palpable in addition to satisfying reinterpretations of what came before.

#21 — BING & SATCHMO (1960)

Favorite track: “Muskrat Ramble”

Crosby and Armstrong’s pairings over the years always carried a joy and sonic fusion that made for great entertainment. The full album they made together, BING & SATCHMO, is no different. Although both aging, Crosby and Armstrong sound vital and in a playful mood, tossing back and forth to each other’s iconic voices with grace. Some of the arrangements on the songs can’t quite match Bing and Satchmo’s energy, but there’s no denying the polish on the album makes it so smoothly fun. BING & SATCHMO was the culmination of decades of collaboration and you can hear the mutual respect on it.

#20 — RETURN TO PARADISE ISLANDS (1964)

Favorite track: “Return to Paradise”

With the ’30s explosion of “South Seas aesthetics” in the west, often in a co-opting manner, Crosby became associated with a whole “Hawaiian music” subgenre. Of course, the style he and his songwriters practiced was a white bread version of whatever inspiration they took, but it didn’t result in terrible music in its own right. Decades later, the crooner went back to this association with RETURN TO PARADISE ISLANDS, which to some extent was able to capture the dreamy atmosphere of those earlier efforts. But there is something lacking in the production quality (in spite of Nelson Riddle’s arrangement) that makes the album somewhat out of step with the magic of a “Sweet Leilani,” for instance. Still, RETURN TO PARADISE ISLANDS is an impressively relaxing and affecting piece in the midst of Crosby’s early ’60s work, and indeed, in the whole scope of his discography.

#19 — FANCY MEETING YOU HERE (1958)

Favorite track: “Fancy Meeting You Here”

Although they had starred together, Crosby and Clooney weren’t paired on the “commercial recordings” of WHITE CHRISTMAS’ songs due to record label commitments. But a few years later, they were able to get together to make this freewheeling, globe-trotting bit of jazzy pop. FANCY MEETING YOU HERE’s concept can sometimes get a little tired, but the songwriting hooks on display for the selected tunes, to say nothing of Crosby and Clooney’s voices in fine form, make it an album with staying power.

#18 — BLUE OF THE NIGHT (1948)

Favorite track: “Where the Blue of the Night (Meets the Gold of the Day)”

BLUE OF THE NIGHT was a collection of love songs delivered in crooning balladic fashion. Even by Crosby standards, the tracks can sound pretty old-fashioned. But there is something remarkable about the serenity that comes through the ages for this set, especially on the (semi) title track. BLUE OF THE NIGHT captures the ethereality that the best early Crosby work had.

#17 — GO WEST YOUNG MAN (1950)

Favorite track: “Have I Told You Lately That I Love You?”

I mentioned the Andrews Sisters earlier in the context of an album that only partly featured them, but GO WEST YOUNG MAN once again brought them to Crosby with a country-inflected tone, and in full force. Every song sees Crosby and the Sisters weaving incredible harmonies with softness, as on “Have I Told You Lately That I Love You?” (a nostalgic favorite), and deft energy, as on “Along the Navajo Trail.” As one of the few Crosby albums dedicated to his work with the Andrews Sisters, GO WEST YOUNG MAN excels.

#16 — COLLECTORS’ CLASSICS — VOL. 1 (1951)

Favorite track: “It’s Easy to Remember”

The best of the COLLECTORS’ CLASSICS albums reaches the furthest back in time. Featuring songs from HERE IS MY HEART (1934), THE BIG BROADCAST OF 1936 (1935), and MISSISSIPI (1935), VOL. 1’s style comes closest to the Al Jolson/Eddie Cantor emulation that Crosby was kind of striving for in the earliest years of his career. His voice is certainly the highest you’ll hear it than at any later point in his career and that offers its own sort of appeal. Ultimately, COLLECTORS’ CLASSICS — VOL. 1 nearly offers the best crop of songs within the compilation series, reflecting the quality of early Crosby musical work high among the releases of the rest of his career.

#15 — BEAUTIFUL MEMORIES (1977)

Favorite track: “Beautiful Memories”

BEAUTIFUL MEMORIES is the best of Crosby’s last string of albums, which he made in London right at the end of his life. Although it wasn’t his absolute last, it more effectively communicates SEASONS’ themes. Stronger pop hooks on the more upbeat songs (like the title song) and more affecting quiet moments make the record a testament to Crosby’s legacy, albeit in an indirect way. BEAUTIFUL MEMORIES does indeed feature many beautiful sounds, enveloping Crosby’s aged but still smooth voice.

#14 — COWBOY SONGS (1939)

Favorite track: “Take Me Back to My Boots and Saddle”

On the other end of the spectrum, COWBOY SONGS was Crosby’s first album, albeit a compilation that gathered recent country-western hits. Sound familiar? The difference with this early effort is that the songs hum with that unnamable frequency I’ve referred to when writing about the ’30s and ’40s work. The orchestration and the technology’s ability to capture it funnels the music into an often dreamlike space, and in Crosby’s case, his voice was the cherry on top. COWBOY SONGS is on the whole not an electrifying collection of tunes, full of high energy as may otherwise be expected. A few songs hit an upbeat tempo, but the record’s most impressive moments are its descents into slow, quiet spaces that evoke loneliness in the wilderness. COWBOY SONGS feels prehistoric in a way and that’s precisely why I love it.

#13 — STAR DUST (1940)

Favorite track: “Star Dust”

Like COWBOY SONGS, STAR DUST is essentially a bundle of sentimentality. Relying on the success and tone of its hit title single, the whole compilation soars into spacey-ness with Crosby’s warbling tones. STAR DUST is nearly peak “early” Crosby (even though it came out 13 years after his recording career began), channeling a protolithic era of pop music into music that is soothing and magical to this day.

#12 — WHITE CHRISTMAS (1954)

Favorite track: “White Christmas”

The Michael Curtiz-directed WHITE CHRISTMAS film is not where the song of the same name debuted. It did, however, capitalize on the success of the song from HOLIDAY INN (1942) 12 years later. And a pretty good movie came out of it. The corresponding album mirrors the way “soundtrack” records were made at the time. Studio settings were more controlled than film sets (and their accompanying sound spaces), so the songs were replicated separately for the album. And in the process, record label commitments came to light. Therefore, although she starred in the film, Clooney was replaced by Peggy Lee on the WHITE CHRISTMAS album. Although Clooney’s presence is missed, it’s not enough to totally sink the whole effort, especially since Lee is a great vocalist herself. Carrying top-tier movie musical number cheese, the songs on WHITE CHRISTMAS are nevertheless consistently entertaining and lively and are in fact almost entirely not Christmas-centric. But when it all culminates in the choral arrangement of the title song (admittedly not as heavenly as it sounds in the film version), the spirit and good nature of WHITE CHRISTMAS is driven home.

#11 — COLLECTORS’ CLASSICS — VOL. 4 (1951)

Favorite track: “Sweet Leilani”

Admittedly, there’s a little cheating with placing COLLECTORS’ CLASSICS — VOL. 4 this high on the list. Half of it is dedicated to songs from WAIKIKI WEDDING (1937), the movie that jumpstarted Crosby’s “Hawaiian image” and which holds a number of songs that appeared on an earlier compilation and that have brilliant backing vocals and instrumentation. But the other half of VOL. 4, comprised of tracks from DOUBLE OR NOTHING (1937), is also a magical sojourn, albeit one of a different flavor. Ultimately, COLLECTORS’ CLASSICS — VOL. 4 represents the peak of the project to compile the best songs from Crosby’s early film career, and as such, it also stands as one of his best albums on its own accord.

#10 — ANYTHING GOES (1956)

Favorite track: “Anything Goes”

The 1956 film version of ANYTHING GOES was Crosby’s second run at the material…kind of. While the 1936 movie was relatively faithful to the stage production, the remake kept the songs and not much else. But oh what songs. Crosby, Donald O’Connor, Mitzi Gaynor, and Zizi Jeanmaire do justice to an over-the-top set of songs. The ANYTHING GOES album almost never lets up (with the exception of the questionable “A Second Hand Turban and a Crystal Ball”); even the orchestral sojourn is a welcome, dreamlike change of pace. The title song is one of those all-time catchy showtunes and it anchors the whole of ANYTHING GOES, a top ten Crosby album.

#9 — HEY JUDE/HEY BING (1969)

Favorite track: “Little Green Apples”

Singing “Little Drummer Boy” with David Bowie wasn’t Crosby’s only crossover with 1960s and ’70s counterculture. He covered The Beatles for HEY JUDE/HEY BING, in addition to tackling a bushel of other modern tunes. Although the “Hey Jude” rendition initially rankled me, repeat listens swayed me to its cause. But Crosby’s cover of “Little Green Apples” has become one of my favorite Bing tunes period. It’s such a lush and wonderful version, although as with the rest of the album, the mix threatens to drown out the vocalist. HEY JUDE/HEY BING is a surprising late career success, an experiment in contemporary trends while retaining a classical pop sensibility.

#8 — CHRISTMAS GREETINGS (1949)

Favorite track: “Here Comes Santa Claus”

CHRISTMAS GREETINGS isn’t much more than another Crosby Christmas album in terms of its approach and collection of songs. But at this earlier stage in his career, his voice is in fine control, the instrumentation is still classically poppy, and the Andrews Sisters join him on a couple songs. CHRISTMAS GREETINGS is pure nostalgia candy, perhaps too saccharine for some, but nearly as satisfying as holiday music can get for me.

#7 — UNDER WESTERN SKIES (1941)

Favorite track: “Empty Saddles”

Yet another country-western-themed album from Crosby’s early years, UNDER WESTERN SKIES nevertheless joins the ranks of soul-stirring ballads rather than standing as an also-ran. The collection of ten tracks don’t veer too much from each other in terms of tone, but Crosby’s ability to hit the higher notes melds with the steel guitar, ghostly strings, and belting choral backing. UNDER WESTERN SKIES achieves the creation of the sensation of open spaces and our small mark on them.

#6 — CROSBYANA (1941)

Favorite track: “It’s Easy to Remember”

CROSBYANA is a compilation of a few Bing movies and in pulling together hits from early filmic successes it ended up standing as one of his finest albums. Succinctly and powerfully channeling the qualities of the ’30s work I’ve already praised, CROSBYANA is, fittingly enough considering the cultivation of a “sensation” of Bing Crosby the title provides, one of a few perfect entry points to his appeal.

#5 — BLUE SKIES (1946)

Favorite track: “Puttin’ on the Ritz”

The Technicolor film BLUE SKIES was a reteaming of Crosby and Astaire and it famously associated the dancer-singer with “Puttin’ on the Ritz” for the rest of his career. It’s so enduring, in fact, that the Astaire solo outshines any of the Crosby contributions to the BLUE SKIES album, although it must be said the title track is a close second. Indeed, this dichotomy illustrates the beauty of the record. The high-energy jazz of “Puttin’ on the Ritz” is just as memorable as the slow, emotional ballads like the opening song. BLUE SKIES is able to bridge the gap between its two tentpole songs with fun and yearning, making it one of Crosby’s (and Astaire’s) finest albums.

#4 — DRIFTING AND DREAMING (1947)

Favorite track: “Where the Blue of the Night (Meets the Gold of the Day)”

DRIFTING AND DREAMING is one of those Decca collections that kind of loosely interpreted a theme; in this case, songs that deal with serenity and, well, dreams. It’s a bit thin, but the songs selected for such a premise are among Crosby’s best, at least assembled in this fashion. DRIFTING AND DREAMING is a beautiful tone piece, an embodiment of the words I’ve been searching for for much of this piece, that description of what makes Crosby’s old, out-of-time ballads so emotional to this day.

#3 — FAVORITE HAWAIIAN SONGS (1940)

Favorite track: “Sweet Leilani”

FAVORITE HAWAIIAN SONGS has a place in history as part of the mass exoticism that came to the islands. I have a feeling its music is about as “Hawaiian” as Taco Bell’s food is “Mexican.” But as with Taco Bell, this bastardized interpretation is ultimately satisfying. FAVORITE HAWAIIAN SONGS actually operates with a restrained hand for most of its runtime, swirling with magic energy conjured up by the angelic choruses (best heard on “Sweet Leilani”) and rippling steel guitar. The album’s commitment to the sensations offered by these elements is also impressive. As dismissive as I’ve somewhat been to the Decca concepts, these extremely early efforts to provide cohesive musical experiences in album form were novel. And to this day, a record like FAVORITE HAWAIIAN SONGS can be spun in its entirety and conjure up sounds that can’t quite be replicated today.

#2 — MERRY CHRISTMAS (1945)

Favorite track: “White Christmas”

In researching Crosby and his work for this piece, I learned that the version of “White Christmas” often heard isn’t even the original. At some point, the master for the 1942 hit wore out from so many re-pressings that Crosby and Co. (the same backing choir, band, everyone) replicated the tune as closely as possible. Subsequent reissues of MERRY CHRISTMAS, Crosby’s first Christmas album, were retitled WHITE CHRISTMAS (as if there weren’t enough things called that already) and carries the 1947 re-recording. But at the end of the day, that version is still quite beautiful. And indeed, the rest of MERRY CHRISTMAS carries a lot of standards that make it a lasting masterpiece in the holiday genre.

#1 — HOLIDAY INN (1942)

Favorite track: “White Christmas”

When I say holiday genre, I guess HOLIDAY INN is the most fitting example. Famously associated with the song it debuted, “White Christmas,” the soundtrack for the film of the same name only deals with the December holiday in that track and “Happy Holiday.” Otherwise, it charts a whole year’s worth of commemorations with songs written by Irving Berlin. Even though I’ve written positively about Crosby’s Christmas music, I am shocked at how much of it appeared high on this list. As I noted in my introduction, I am not typically a Christmas music person. But when it echoes through time in this classically pop way, fueling my nostalgia for the holiday as a child at my grandparents’ house, it’s hard to beat. And ultimately, HOLIDAY INN is not a huge success purely because of “White Christmas.” Astaire’s accompaniment adds a welcome voice into the mix with Crosby, while the energy across the track list is phenomenal (except for “Abraham,” rendered as a minstrel show number in the film). HOLIDAY INN stands as, I think, a crucial conduit to the world of old pop music, if such a realm is somewhere one would ever want to go. “White Christmas” is the doorway, but Berlin’s talents were on full display on this album, as are Crosby’s of course. The singer may have sounded better, or his backing instrumentation may have come off as more otherworldly, or his approach to an album was maybe more radical here and there. But HOLIDAY INN really is Bing Crosby at his finest, the best album to come out of a remarkably long and prolific career.

And now, the rest of this vast list…

#102–101 GANG SONGS (1961)

Favorite track: “Heaven, Heaven/Mary, Don’t You Weep/Jacob’s Ladder/Nobody Knows the Trouble I’ve Seen/Roll, Jordan, Roll”

#101 — JOIN BING AND SING ALONG (1960)

Favorite track: “Daisy Bell/The Bowery/After the Ball”

#100 — ON THE HAPPY SIDE (1962)

Favorite track: “Should I? (Reveal Exactly How I Feel)/Blue Moon”

#99 — BELOVED HYMNS (1951)

Favorite track: “Rock of Ages”

#98 — THE ROAD TO HONG KONG (1962)

Favorite track: “Let’s Not Be Sensible”

#97 — STEPHEN FOSTER (1946)

Favorite track: “Beautiful Dreamer”

#96 — BALLAD FOR AMERICANS (1940)

Favorite track: “Part IV”

#95 — AULD LANG SYNE (1948)

Favorite track: “Now Is the Hour”

#94 — ON THE SENTIMENTAL SIDE (2010)

Favorite track: “If I Didn’t Care/Blueberry Hill”

Note: the only posthumous release on this list, as it was a completed album recorded in 1962 but never released.

#93 — AMERICA, I HEAR YOU SINGING (1964)

Favorite track: “The House I Live In”

#92 — GARY CROSBY AND FRIEND (1953)

Favorite track: “Play a Simple Melody”

#91 — BING CROSBY SINGS WITH LIONEL HAMPTON, EDDIE HEYWOOD, LOUIS JORDAN (1948)

Favorite track: “Baby, Won’t You Please Come Home”

#90 — HIGH TOR (1956)

Favorite track: “John Barleycorn”

#89 — SAY ONE FOR ME (1959)

Favorite track: “Say One for Me”

#88 — EL SEÑOR BING (1961)

Favorite track: “Malaguena (At the Crossroads)/Andalucia (The Breeze and I)”

#87 — WELCOME STRANGER (1947)

Favorite track: “Smile Right Back at the Sun”

#86 — THE EMPEROR WALTZ (1948)

Favorite track: “The Emperor Waltz”

#85 — TOP O’ THE MORNING (1950)

Favorite track: “Top o’ the Morning”

#84 — BING CROSBY AND THE ANDREWS SISTERS (1953)

Favorite track: “Ciribiribin”

#83 — YOURS IS MY HEART ALONE (1951)

Favorite track: “I Kiss Your Hand, Madame”

#82 — ROAD TO BALI (1952)

Favorite track: “Road to Bali”

#81 — THE COUNTRY GIRL/LITTLE BOY LOST (1955)

Favorite track: “Violets and Violins”

#80 — BING SINGS WHILST BREGMAN SWINGS (1956)

Favorite track: “Nice Work If You Can Get It”

#79 — BING WITH A BEAT (1957)

Favorite track: “Along the Way to Waikiki”

#78 — BING SINGS THE GREAT COUNTRY HITS (1965)

Favorite track: “Sunflower”

#77 — COLLECTORS’ CLASSICS — VOL. 8 (1951)

Favorite track: “If I Had My Way”

#76 — SONGS I WISH I HAD SUNG THE FIRST TIME AROUND (1956)

Favorite track: “April Showers”

#75 — ST. PATRICK’S DAY (1947)

Favorite track: “The Rose of Tralee”

#74 — EL BINGO (1947)

Favorite track: “Siboney”

#73 — VICTOR HERBERT (1947)

Favorite track: “Ah! Sweet Mystery of Life”

#72 — SMALL FRY (1941)

Favorite track: “Poor Old Rover”

#71 — COUNTRY STYLE (1951)

Favorite track: “Country Style”

#70 — BING ’N’ BASIE (1972)

Favorite track: “Little Green Apples”

#69 — NEW TRICKS (1957)

Favorite track: “Georgia on My Mind”

#68 — SOME FINE OLD CHESTNUTS (1954)

Favorite track: “Dinah”

#67 — BINGO VIEJO (1977)

Favorite track: “Eres tú”

#66 — HOW THE WEST WAS WON (1960)

Favorite track: “Green Grow the Lilacs”

#65 — BING SINGS THE HITS (1954)

Favorite track: “I Love Paris”

#64 — WHEN IRISH EYES ARE SMILING (1952)

Favorite track: “Eileen”

#63 — A CONNECTICUT YANKEE IN KING ARTHUR’S COURT (1949)

Favorite track: “Once and for Always”

#62 — MR. MUSIC (1950)

Favorite track: “Life Is So Peculiar”

#61 — BING CROSBY’S TREASURY — THE SONGS I LOVE (1968)

Favorite track: “One for My Baby”

#60 — AT MY TIME OF LIFE (1976)

Favorite track: “Heat Wave”

#59 — COLLECTORS’ CLASSICS — VOL. 6 (1951)

Favorite track: “This Is My Night to Dream”

#58 — BING CROSBY SINGS THE SONG HITS FROM… (1951)

Favorite track: “Big Movie Show in the Sky”

#57 — BING CROSBY SINGS THE SONG HITS FROM BROADWAY SHOWS (1948)

Favorite track: “People Will Say We’re in Love”

#56 — COLLECTORS’ CLASSICS — VOL. 7 (1951)

Favorite track: “East Side of Heaven”

#55 — BING CROSBY SINGS COLE PORTER SONGS (1949)

Favorite track: “Easy to Love”

#54 — ST. VALENTINE’S DAY (1948)

Favorite track: “I’ll Be Seeing You”

#53 — BING AND THE DIXIELAND BANDS (1951)

Favorite track: “Walking the Floor Over You”

#52 — BING AND CONNEE (1952)

Favorite track: “An Apple for the Teacher”

#51 — ROAD TO RIO (1948)

Favorite track: “But Beautiful”

That’s all, folks!