Jorma Taccone, Andy Samberg & Akiva Schaffer of The Lonely Island.

The Five Best Lonely Island Movies Ranked

Jorma Taccone, Andy Samberg & Akiva Schaffer of The Lonely Island.
Jorma Taccone, Andy Samberg & Akiva Schaffer of The Lonely Island.

The fan favorite comedy trio, The Lonely Island (comprised of Andy Samberg, Akiva Schaffer & Jorma Taccone), has come a long way since meeting in middle school & moving to New York to help pave the way for musical & sketch comedy in the digital landscape via their viral and hysterical Saturday Night Live Digital Shorts. Their early hits, Lazy Sunday & Laser Cats, gave them the opportunity to work on their first feature film, Hot Rod. Later catapulting them into stardom releasing four studio albums as a musical comedy trio and now running a full fledged production company where they produce, write, direct & star in leading comedy films & television shows beyond SNL (including Tim Robinson’s I Think You Should Leave & Comedy Central’s animated series Digman! to name a few).

The trio’s newest project premiering on Hulu this month is a new comedy thriller they produced, Samberg plays in and marks Jake Johnson’s directorial debut (where he also stars) called Self Reliance. To mark the latest addition to the Lonely Island universe, the 800 Pound Gorilla News Staff got together, picked five of their best films and ranked them here as best as we could to look back at the trio’s impact on comedy & culture.

5) Chip n’ Dale: Rescue Rangers

If someone told us that The Lonely Island would be tapped to lead the most meta animation crossover, fourth wall breaking, cameo & Easter egg heavy movie to have been created so far and that it came from the studio helmed by the House of Mouse, we certainly would not have had that on our Bingo card (and we couldn’t be more thrilled about it). In the short time since it’s been released, it continues to be an unforgettable film that stands out in the most enjoyable ways as the trio’s film catalog continues to grow.


Akiva Schaffer directs, Andy Samberg stars as Dale, and Jorma Taccone fills some various voice roles including Batman & the Toon Car. The team helps tell the story of Chip & Dale (played by John Mulaney & Samberg respectively) since the cancellation of Rescue Rangers from decades ago now set in modern day and the duo’s mission to save their friend who’s been kidnapped while also working to repair their broken friendship. It’s got plenty of obvious qualities for a Lonely Island film: a spontaneous rap song in the vein of their SNL digital shorts, Samberg’s charisma & charm in his characters, and its classic fourth wall breaking.


For a nearly kid focused movie (a nearly perfect all ages film), it’s got quite possibly one of the most stacked comedy casts in a true form Disney film to exist yet. Including Mulaney & Samberg, you have Keegan-Michael Key, Will Arnett, Tim Robinson, Chris Parnell & Seth Rogen all voicing some odd & left of center characters that come from this populated crossover experience. For further context, it’s crazy looking back in the relatively short time since it recently came out how crazy these crossovers were pulled off like Randy from South Park, Beavis And Butt-head (again, a kids movie), Jimmy Neutron, and even crazier, Seth Rogen interacting as himself as four different characters he’s played in different animated universes. No one could ever imagine the legal sign offs that had to go on to get this film approved for each appearance (even for just a split second). Overall, a solid & silly nostalgic movie that will have any pop culture fan fully satisfied beyond measure!


How to watch: streaming on Disney+ (of course)!

4) MacGruber

Your enjoyment of this will depend on how much you enjoy the comedy stylings of Will Forte. Neither fish nor fowl for most, Forte can have a tendency to push scenes to their limits in terms of annoyance, and often dances on the edge of cringe or discomfort with glee. Luckily, Forte smartly surrounds himself with capable actors who are willing to match his frequency as a frustrating, unhinged, man-baby action hero with a love of Tazo tea and one abortion to his name. Between the absurdity of the script and the anchoring of Kristen Wiig and Ryan Phillipe (as a “cooler” for Forte’s calculated unhingedness), the film works-ish to wildly varying degrees of success from scene to scene.


The film is in the four spot here for the good comedy that breaks through, sure, but also for its ambition. The film is set-piece after set-piece, with Phillipe being used as a human shield as gun-fire rains down in one scene, and Wiig struggling through a cafe order in another, and an all-out battle in the next. Val Kilmer takes a villainous turn, finding more comedy than evil in his performance, but still fun nonetheless. This film might be for you, but either way it’s a cult classic in the truest sense (directed, produced & written by The Lonely Island).


How to watch: available on Prime Video!

3) Popstar: Never Stop Never Stopping

By the time The Lonely Island collaborated for their second feature film, they were already big names in the world of comedy music, thanks to the success of their albums. So it would stand to reason that the trio would find a way to incorporate that into their next project.


Produced by Judd Apatow and directed by Akiva Schaffer, Popstar: Never Stop Never Stopping wears many hats. It’s a send-up of the popular concert documentaries from the likes of Justin Bieber and One Direction. It follows a boy band that breaks up when one member goes solo, taking all the credit for himself. It features hilarious performances from Tim Meadows, Sarah Silverman, Maya Rudolph, Joan Cusack, and cameos from Justin Timberlake, Ringo Starr, Bill Hader, Will Arnett, Chris Redd, Weird Al Yankovic, and countless others.


While not a box office success when it was first released, like Hot Rod, the film found its audience since it came out. If you’re a fan of The Lonely Island, this is definitely one you’ll need to check out.


How to watch: streaming on Hulu!

2) Hot Rod

After getting a big break and killing it on their first two seasons on Saturday Night Live, Lorne Michaels gave this up and coming comedy trio the opportunity of a lifetime to create their first feature length film. And this wasn’t just any movie. Little did they know that they were making a film that would go on to become a true cult classic and undeniably one of the most quotable films continuously referenced in pop culture since it came out in 2007. From the grilled cheese vs. taco debate, who likes to party the most, the safe word WHiskey (however you prefer to pronounce it, you know the right way), to babe wait…BABE, the list goes on and on in the first entry to the Lonely Island universe, Hot Rod.


Lorne produced while Samberg & Taccone star & Akiva Schaffer made his directorial debut. The movie follows an Evel Knievel like stuntman, Rod Kimball (Samberg), who sets out to do the stunt of a lifetime to raise money for his ill step-father’s operation. While this movie is not perfect and is not and doesn’t always make complete sense, that’s just exactly what fans appreciate in these guys’ style. This movie is incredibly silly, slapsticky and filled with so much absurdity that only true Lonely Island fans will appreciate. It’s also great to note how great this cast has aged since its release nearly 17 years ago. Bill Hader, Danny McBride, Isla Fisher, Chris Parnell & Will Arnett have all gone on to become some of the biggest, talented & still successful comedic actors since making this truly comedy gold flick.


How to watch: available on Prime Video!

1) Palm Springs

When you think of time warp movies - where your lead character is stuck in a never-ending time loop - the first film you may think of is 1993’s Groundhog Day. In that film, you see Bill Murray play someone who is desperate to escape the time loop and - spoiler! - emerges a changed man by the end. For as many films that have tried to adopt a similar principle since then, there’s one time loop movie that seemingly stands out above the rest.


Palm Springs is a film that finds Andy Samberg repeating the same day over and over again, which is the day of a wedding in Palm Springs. He encounters a fellow wedding goer, who after spending the night together, accidentally follows Samberg into the time loop. Instead of being a character evaluation of Samberg, instead we see two characters who just sort of accept their fate and eventually seem content to live each day doing whatever they want with no consequences. The film is expertly directed by Max Barbakow based on a script from Andy Siara. Samberg and his co-star Cristin Milioti share a pretty solid chemistry that makes this high-concept time loop movie really work.


How to watch: streaming on Hulu!

Bonus: The Unauthorized Bash Brothers Experience

As good as Palm Springs? Maybe. Better than Popstar? Maybe. This thirty-minute excursion into the frail homoerotic psyches of baseball legends Jose Canseco and Mark McGwire features the best directing The Lonely Island have ever executed on their own via Bash Brothers. It is a sumptuous feast of visuals that manages to have distinct cinematography and a very distinct color palette that corresponds with different emotional tones Canseco and McGwire try to suppress. This is due in no small part to the amazing work of Mike Diva, who collaborates with Akiva Schaffer on the direction of this art piece. 


The best thing the film does is remind viewers that it doesn’t matter if comedy folks make something hilarious, because the truth is ambition can outpace form. The same guys that made Popstar are not the same guys that made this film, and it is a truly special project because it shows what creativity can look like if artists gamble on sincerity over persona. If you’re looking for a film that uses Sterling K. Brown to silly effect, but features a genuinely stunning, cinematic scene set in a parking lot with the Haim sisters, look no further. Take the ride with The Lonely Island not because they’re funny and you find it soothing to think about them being on SNL as you age, but because they’re maybe the first comedy group to show ambition beyond the genre, and might be a north star for future generations looking to age with grace.


How to watch: streaming on Netflix!

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