The 10 Best Lonely Island Videos

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I keep wanting to call the new Naked Gun “a Lonely Island movie,” but that’s not quite true. While it is co-written and directed by Akiva Shaffer, one member of The Lonely Island, with drafts by Family Guy writers Mark Hentemann and Alec Sulkin, and eventual writing credit shared between Shaffer, Dan Gregor and Doug Mand (My Crazy Ex-Girlfriend), but the other Lonely Island guys (Andy Samberg and Jorma Taccone) don’t seem to be involved.

Does that inconvenient fact shit on the entire premise of this list? MAYBE.

But if there’s one ironclad truth in this God-forsaken world, it’s that you absolutely, positively cannot stop me from wasting an entire day watching 20-year-old YouTube videos. That’s the Mancini Guarantee.

And in any case, there does seem to be an unmistakable whiff of Lonely Island to the new Naked Gun. I’ll get into it more in my review, but basically: no one commits to the bit like the Lonely Island guys. That’s been a throughline of their work since they were in, or barely out of college, way before the movies and the awards show gigs and SNL digital shorts and Netflix specials. They take a really stupid idea and treat it like a megabudget Shakespeare adaptation, using whatever minimal resources they have at hand. Putting all that work into a 3 am idea is what makes the comedy work (the joke behind the joke) and being able to get your friends to help you bring that stupid idea to life makes everything they do a sort of de facto salute to the value of creating stuff with your friends. Most comedy stuff I enjoy tends to have that quality.

I had lots of astute analysis and high-minded questions like this on my mind when I finally got to interview the Lonely Island guys in 2016 during the Popstar tour after following their work for the previous 14 or 15 years. But I threw it all out the window to do an extended dick joke bit. So it goes. Anyway, I don’t regret it.

I was recently accused by a friend of being biased towards creators’ earlier works, and while that’s not entirely true (for instance: Bottle Rocket is one of the worst Wes Anderson movies), I have been watching these dumb videos since I was a dumb college student myself. And as with all comedy, there is an element of “you kinda had to be there” to it. Also, a lot of the earlier stuff made with fewer people involved and less money naturally tends to be dumber, and as Lester Bangs says about rock music in Almost Famous, “the day it ceases to be dumb is the day it ceases to be real.”

I tend to think the same about comedy. I also didn’t deliberately avoid the more obvious “hits” out of a desire to be contrarian. But there is a natural cycle to anything that gets overhyped or overquoted, where you tend to be less excited to relive it. And so I left off things like “Dick in Box” and “Lazy Sunday” and “I’m on a Boat,” even though they were great for their time. File under: great at the time, don’t have to relive.

Wow, have I self-justified and catalogued my caveats enough? It’s a dumb listicle, god why am I still typing.

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10. Ras Trent

Rewatching Ras Trent, it isn’t nearly as laugh-out-loud funny as I once thought, maybe because I watched it way too many times back when it came out. But I had to save it a spot on the list, because it’s one of those sketches I’ve thought about probably once a week since it came out. Every time I remember Matisyahu I think of Ras Trent.

Overall “Ras Trent” is a rare Lonely Island video that’s maybe a little funnier in concept than in execution, but the concept is so undeniably great that the concept ends up being all you remember anyway. He’s Ras Trent!

The backstory for it, recently-ish revealed to Seth Meyers on a podcast, is also pretty great:

While attending Berkeley High, they became big fans of reggae and dancehall music, which led them to go see the classic roots reggae band the Itals, best known for songs like “In A Dis Ya Time” and “Satisfaction,” at a small venue in Petaluma. Samberg didn’t state the name of the venue, but sleuths at the Press Democrat concluded that the event most likely took place at the Phoenix Theater (the Itals also performed locally at the Mystic Theatre, but the staircase doesn’t match the description). It was there that a young Samberg and his friends met the real-life inspiration for Ras Trent in a stairwell after the show.

“This dude who had been at the show walked out, dressed like he was straight out of ‘Office Space,’” said Samberg. “... Khakis tucked in, button-up and glasses. And he just walked up to us and clearly needed to get by, and he just went like, ‘Excuse I.’”

Samberg and his friends couldn’t believe the egregious use of Jamaican Patois. The quote became a running joke, and eventually a punchline in the skit. [SFGate]

“Excuse I” is something that now holds space inside my brain alongside “Ras Trent” itself.

9. Sloths / Like A Boss

“Sloths” feels like the beau ideal of a dumb idea that they somehow managed to make funny through sheer effort and force of will. You can just watch it and know that there’s no cool origin story like the one for Ras Trent. “Heh, yeah, we were kinda just like, ‘what if sloths?’”

The fact that they wrote the line “do cocaine off America’s gravestone” in 2007? Prescient. Those were the pre-financial crisis days. How did they know?

“Like a Boss” lives right on the edge of the “played out” spectrum of Lonely Island videos (anyone remember that someone made a movie called Like a Boss in 2020 starring Tiffany Haddish and Rose Byrne?). At first it seems kind of mid and so random lol, but then Andy sticks the gun in his mouth and chickens out and I sort of laugh uncontrollably at everything else from there. (Threw it on the Ground, which almost made the list, has a similar quality, where it doesn’t quite work until “happy birthday to the ground”).

“So that’s an average day for you, then? You chop your balls off and die?”

8. Peyton Manning for the United Way

It’s easy to forget that the Peyton Manning United Way ad was a Digital Short, seeing as how there are a minimum of goofy effects and no one’s rapping. But it was indeed a Digital Short (another one discussed on a Seth Meyer podcast, which I’ll link even though I think celebrity podcasts are stolen valor).

There are a lot of “cameo makes it funny” type-videos in the SNL canon (a phenomenon that hit its nadir with Celebrity Lip Sync Battle and Carpool Karaoke) but Peyton Manning’s United Way ad was kind of the gold standard. It’s arguably not quite as funny these days, but at the time no one could believe how good he was in it.

7. Space Olympics

I couldn’t not include “Space Olympics,” which is a brilliant concept with incredible costuming where maybe the funniest part of it to me is that it’s a three-minute song that doesn’t actually have that many jokes in it. The obvious water-treading always makes me giggle.

And then it still manages to end strongly. “And as I stare death in the face I know my sins will take me to hell.”

6. Natalie Portman Raps

(superior, uncensored version here)

“Natalie Portman does a foul-mouthed rap” is kind of a corny joke on paper, something AI could easily execute these days, but then she drops bars like “I bust in dudes’ mouths like gushers, motherfucker” and it ends up being undeniable. I didn’t want to put too many “celebrity does funny thing” concepts on this list for reasons already mentioned (less fun to talk about and also genuinely less funny) but “Natalie Raps” was probably the pinnacle of solid sketch-writing colliding with perfect persona then executed to perfection.

What did we say about committing to the bit? Yeah. Natalie Portman didn’t just show up to give it name recognition, she acted her ass off the entire time. This is why she has an Oscar. Even the sequel is pretty good: