The Lonely Island emerged from the early years of the 2000s as a trio of childhood friends making videos for the internet to become SATURDAY NIGHT LIVE (1975-present) innovators and some of the biggest names in comedy. Andy Samberg, Jorma Taccone, and Akiva Schaffer have moved into a universe, simultaneous to their Beastie Boys-inspired comedy rap, full of writing, producing, and directing for projects that don’t precisely bear their name. Of the three, Schaffer has especially built the largest directorial portfolio to date, with six “movie-ish” projects released in the 15 years since 2007. Going through IMDB for the guy, though, you’ll find a lot more, hence my “movie-ish” term to distinguish larger projects from music videos, SNL “digital shorts,” and other contributions to segments of specials. So I’ve written and ranked those six film-like things from Schaffer, often joined by a co-director, who has been in the director’s chair or otherwise involved in some of the best comedy of the past couple decades.
#6 — THE WATCH (2012)
THE WATCH was a big ol’ misfire. A for-hire kind of gig for a long gestating project at least at some point written by Seth Rogen and Evan Goldberg, the sci-fi comedy starred Ben Stiller, Vince Vaughn, Jonah Hill, and Richard Ayoade. It was also Schaffer’s second movie (coming five years after his debut, the biggest gap for him to date) and is absolutely atrocious. Somehow, it feels immensely longer than its 100-minute runtime. THE WATCH is full of immediately unfunny and overdone piss and shit and cum jokes; I’d clock in the total number of laughs or even chuckles or even pleasant smiles it got from me at about three or four. I had totally forgotten about its proximity to the killing of Trayvon Martin by “neighborhood watchman” George Zimmerman, which had led the studio to renaming the movie THE WATCH from “Neighborhood Watch” and focusing the marketing on the alien element. With the lens of that first element, the characters’ interactions with a bunch of high school kids range from creepy to outright terrible. With the lens of that second angle, the movie definitely seems to be going for an R-rated Ghostbusters thing, full of unlikely heroes and whatnot. Instead, THE WATCH just presents a bunch of unlikeable characters doing unfunny things, and unfortunately, Schaffer was behind the camera for all of it.
#5 — THE LONELY ISLAND PRESENTS: THE UNAUTHORIZED BASH BROTHERS EXPERIENCE (2019)
I wrestled with including this visual album on this list, but rather than represent a compilation of various music videos, THE LONELY ISLAND PRESENTS: THE UNAUTHORIZED BASH BROTHERS EXPERIENCE stands as a solidly made and funny short film. Co-directed with Mike Diva, Schaffer also stars as Mark McGwire next to Andy Samberg’s Jose Canseco, portraying baseball’s titular Bash Brothers in the most ridiculous way. THE UNAUTHORIZED BASH BROTHERS EXPERIENCE (2019) is correspondingly The Lonely Island’s most bizarre record, a concept that is mostly consistently funny but doesn’t always yield the best tracks to come from the group. That being said, the songs are entertaining, and they’re better served by the over-the-top visuals Schaffer and Diva deliver for the visual album. The group jokes about BASH BROTHERS being a “visual poem” at the top of the short, but the interstitial moments between the songs are actually pretty beautiful and visually interesting, and are indeed buoyed by the overtly ridiculous nature of the whole piece.
#4 — MICHAEL BOLTON’S BIG, SEXY VALENTINE’S DAY SPECIAL (2017)
Like BASH BROTHERS, MICHAEL BOLTON’S BIG, SEXY VALENTINE’S DAY SPECIAL isn’t in a typical movie form. But hey, it was a standalone comedy special directed by Schaffer (and Comedy Bang Bang’s Scott Aukerman). And most importantly, it’s funny. Continuing the outrageous Lonely Island collaboration trend with soft rock icon Michael Bolton, this hour-long variety show plays with a conceit that could get old real fast. Bolton, asked by Santa to make sure enough babies are born by Christmas to make up for a surplus of toys, hosts a Valentine’s Day special to put people in the sex-having mood. Schaffer and Aukerman are surprisingly able to keep this idea alive throughout the hour, but like many variety shows and specials, this one leads with its best sketches and biggest laughs. The guest star cameos and segments are entirely a delight, and on the whole, MICHAEL BOLTON plies its bizarre concept, characters, and sense of humor with a proficiency that saves the effort from being a joke in name only.
#3 — CHIP ‘N DALE: RESCUE RANGERS (2022)
Schaffer’s latest directorial effort and the impetus for this piece, CHIP ‘N DALE: RESCUE RANGERS is a post-post-modern reboot and WHO FRAMED ROGER RABBIT (1988), um, you could say homage. CHIP ‘N DALE falls into some of the same traps these reverential and referential nostalgia bombs often do (such as panning and focusing on some random character for too long as if to say “hey, remember this guy!”), but it’s surprisingly refreshing and successful in crossing over a million “IPs,” including many outside Disney’s immediate uber-power. In fact, I was impressed/confused how Disney was able to get around the inclusion of characters like “Ugly Sonic” (voiced incredibly by Tim Robinson). Regardless of those meta pieces, CHIP ‘N DALE also succeeds in being a good and funny movie in its own right, though of course much of its appeal comes from its recognition of many, many other characters who originally had nothing to do with Chip ‘n Dale. It was kind of hard to get past John Mulaney and Andy Samberg as the voices; I like them but it just…really…was them as these iconic cartoon characters. In any event, Schaffer and his Lonely Island compatriots were able to bring to the director’s first PG effort their sense of bizarre humor, and doses of more “mature” humor, that makes CHIP ‘N DALE potentially appealing to children and adults.
#2 — HOT ROD (2007)
HOT ROD was The Lonely Island’s first film project and Schaffer’s directorial debut. At its center is Andy Samberg as an aspiring stunt driver who has an incredibly intense and hilarious relationship with his stepfather. The plot of the movie is a clever send-up of the ridiculous plots of many 1990s and early 2000s comedies (BLACK SHEEP  comes to mind) and its execution makes HOT ROD one of the best comedies of its decade. I remember seeing it when it came out and being enamored, as many others were, with “cool beans.” But now, I see it as a nearly definitive example of The Lonely Island “aesthetic,” if you like. HOT ROD is an entirely funny goofball comedy, an antidote to the dominant style comedies of its day and to come (ahem Judd Apatow ahem), that isn’t without heart and certainly not without refinement.
#1 — POPSTAR: NEVER STOP NEVER STOPPING (2016)
POPSTAR: NEVER STOP NEVER STOPPING is one of my favorite movies of all time. Like, top 20 or something. It’s really the second of two Lonely Island movie projects so far, by which I mean all three of the guys are centrally involved and performing a la HOT ROD. And although HOT ROD is great, POPSTAR is a near-perfect comedy. The pop mockumentary style is such a perfect medium for Andy Samberg’s brand of goofy idiot, in this case an amalgamation of figures like Justin Bieber, Drake, and others into the immaculate celebrity dumbo Conner4real. There are so many laugh out loud funny moments in POPSTAR that I’m containing smiles reminiscing about the contenders for the movie’s funniest scenes as I write this. As is the case with The Lonely Island’s best work, and indeed Schaffer’s best as a director, POPSTAR is not just riotously funny, but also humane. The central story of three guys who split up after early success (actually, a theme repeated in CHIP ‘N DALE) could have been the shoehorned emotional component for what was otherwise supposed to be a joke-a-second comedy. Instead, POPSTAR is a joke-a-second comedy and a celebration of male friendship, a movie so funny and charming that it is, in my eyes, quite obviously Schaffer’s best.