Every Lonely Island Music Video, Ranked


With Popstar: Never Stop Never Stopping hitting theaters today, this seemed like a good time to look back at the musical history of The Lonely Island. For more than a decade, these guys have been making hilarious videos and parodies that have mocked pretty much every trend in popular music, while also providing some astute social commentary. They’ve covered a lot of ground, and today, we’re looking at every single music video the group has made. To be clear, we’re only looking at songs they’ve formally released on albums, so non-musical digital shorts were left off the list. Now then, let’s start the arguing!

28. “We Like Sportz”

This was one of the band’s earlier tracks featuring the recurring characters of the 2 Normal Guys. It’s reasonably funny, although the joke here is sort of an obvious one: guys like sports, and sometimes they take it a bit too seriously. Still, the low-on-purpose production quality is enough to make it fairly amusing. Plus, is that a JaMarcus Russell jersey? Now that’s funny! Keep in mind, because this one is last on the list, there basically isn’t a single Lonely Island song that isn’t at least somewhat enjoyable. Their consistency has been stunning.

27. “Jizz in My Pants”

One of the earlier videos, and one of the first hints that The Lonely Island were an actual music group with comedic influences rather than purely a novelty act. This one is reasonably funny, mostly because of Samberg’s delivery, but the only real joke here is that the word “jizz” is funny. They were onto something, but they would go onto better things.

26. “3-Way (The Golden Rule)” featuring Justin Timberlake and Lady Gaga

The third installment of the Timberlake-Samberg series, and probably the weakest, even though it’s not without its charms. This song reveals that the “Dick in a Box” crew is at least a little bit bicurious, as they claim that it’s “not gay if it’s a three-way.” In this case, the joke isn’t *quite* as funny as it was in the first two Timberlake collaborations, but it’s a fun song nonetheless, and Lady Gaga’s presence certainly livens things up a bit.

25. “We’ll Kill U”

This is fairly similar to “We Like Sportz” in terms of its premise with the 2 Normal Guys; both songs are defined by making strong statements with a mundane, detached delivery, but this one is a little bit funnier, mostly because it’s less preachy, and a bit sillier. It’s just two extremely non-threatening beta males saying that’ll they’ll kill you. It gets the job done.

24. “Boombox” featuring Julian Casablancas

This one has a simple premise — the idea that if you start playing a boombox in a random place, everyone will start dancing is ridiculous — but it pulls it off mostly due to a killer chorus from Julian Casablancas. Not sure if this is one of the funnier songs The Lonely Island have ever done, but it’s just a really good song.

23. “Go Kindergarten” featuring Robyn, Diddy, and Paul Rudd

This song mocks yet another tired pop music cliche — the command song, i.e. songs that spend the whole time telling you what do — by pointing out that these songs are basically a game of Simon Says. The song commands people to “make your butt flat” and “punch your friend in the face,” and the oblige because, well, the song told them to. The mindless of modern pop summed up perfectly.

22. “I Just Had Sex” featuring Akon

At times, The Lonely Island are less of a comedy act, and more of a legitimate pop/rap act that just happens to tell jokes. That was never more true than with this song that actually became a top 40 hit. Akon was the perfect one to sing the hook, especially when you consider that he once topped the charts with a song literally called “I Wanna F*** You.”

21. “When Will the Bass Drop”

If the dubstep phenomenon has left you annoyed confused, this is the song for you. We watch Samberg play an Avicii/Deadmau5 type who collects bags full of money while doing nothing but making his audience wait for the bass to drop. The part where he starts frying an egg is especially good.

20. “I’m on a Boat” featuring T-Pain

One of the group’s most ubiquitous songs — chances are, at some point in 2009, you or one of your Facebook friends had “I’M ON A BOAT” as your status. But while this one was around a lot, it never wore out its welcome. This was at the peak of T-Pain’s autotune-driven popularity, and it showed he had had a sense of humor about himself, as hip-hop’s boastful nature is lovingly skewered here.

19. “YOLO” featuring Adam Levine and Kendrick Lamar

In early 2013, the word “YOLO” was was annoying the entire universe, as Drake’s catchphrase had spiraled out of control, being used by just about everyone. Thankfully, The Lonely Island came to the rescue by turning the expression on its head. While it’s true that you only live once, this song argues that this is actually a reason to be extremely cautious, because YOLO could also stand for “you oughta look out.” Worth noting, this was actually Adam Levine’s second time working with the band, after “Iran So Far,” which never made any of the band’s albums.

18. “Shy Ronnie 2: Ronnie and Clyde” featuring Rihanna

Rihanna reprises her role from the original sketch, which has now been fleshed into a big-budget video, not much different from what you’d expect from one of her singles. The joke is the same — Shy Ronnie is too shy for anyone to hear him — but by bringing it in the context of a Bonnie & Clyde-style bank-robbery, the crew are able to get some more laughs onto the premise. Rihanna’s deadpan delivery of “no one in the back can hear you” is particularly good.

17. “We Need Love”

The follow-up to “We Like Sportz” and “We’ll Kill U,” and easily the funniest of the bunch, as the two guys tell us what they look for in a woman in the most deadpan way possible. As the song goes on, it becomes clear they have some questionable attitudes about women, which, as usual, they state in the most dry, matter-of-fact way possible. This saga definitely ended with its funniest installment.

16. “Natalie’s Rap

After the massive success of “Lazy Sunday,” this was essentially the sequel, and it was a fun bit as Natalie Portman showed us that she wasn’t quite the good girl she had often been perceived as. Portman, Samberg and Chris Parnell all get in some good lines here, although I’ll say that Samberg telling Portman “my dick is scared of you” is usually the part that gets the biggest laugh from me.

15. “Space Olympics”

One of the group’s most surreal videos, this song features several non-sequiturs, as the phrase “you’re a winner” is repeated throughout, without ever having much of a clear meaning. The song describes what the sci-fi influenced idea of what the Olympics might look like somewhere in the distant future. But hey, with the all the issues in Rio, we might have to move the Space Olympics up a millennium or two.

14. “Hugs” featuring Pharell and Tatiana Maslany

It’s amazing how good these guys are at making one joke really, really funny. The premise in this song is simple — replace the word “f***”, or any other word that could be used as slang for sex — and replace it with “hug.” It shouldn’t be so damn funny, but it is, possibly because of the conviction the guys deliver the lines with, particularly the opening warning that “we are not gentleman.” It’s not the most complex humor in the world, but it gets the job done.

13. “The Creep” featuring Nicki Minaj

One of The Lonely Island’s biggest strengths is their ability to mock certain unfortunate male behaviors without coming off as especially preachy. On “Spring Break Anthem,” for example, they poke fun at men acting macho and sexist as a way of covering up insecurities about their sexuality. Here, they set their sights on guys who try to start conversations with women in the most awkward way possible by giving us a new dance move: The Creep. This is a case where the video really makes the song work, as the band’s movements are gloriously ridiculous here. Of course, girls can get in on the creeping action, too, as Nicki Minaj comes in with a strong guest verse.

12. “Reba (When Worlds Collide)” featuring Kenan Thompson

This one could be described as a bit of a high-concept video: Andy Samberg is collaborating with Reba McEntire…except it’s actually Kenan Thompson in drag. This idea is funny enough already, but it gets better (and more awkward) when the pair rap about having sex. The Lonely Island have long been great at turning absurd concepts into hilarious songs, and this is a perfect example of it.

11. “Motherlover”

The sequel to “Dick in a Box” — it starts with Samberg and Timberlake getting out of jail for their lewd acts — “Motherlover” is slightly less charming than the original because it used modern beats rather than the early ’90s vibe that made its predecessor so great. Still, the idea of two guys planning to have sex with each other’s moms as a Mother’s Day present is hilarious for obvious reasons, and that’s enough to propel “Motherlover” fairly high on the list.

10. “Like a Boss” featuring Seth Rogen

This one starts out by inverting the hip-hop idea of a Boss with the rather mundane tasks that an actual boss has to go through (writing memos and the like), but from there, the song becomes increasingly dark and surreal. There’s a madcap energy to this song that makes it impossible not to enjoy. Also fun is Seth Rogen’s performance as the boss’ boss.

9. “Diaper Money

The Lonely Island are incredibly skilled at inverting hip-hop tropes, and this is a fine example of that. The group first brags about having stacks of cash to spend… on diapers. Then, we get a verse about getting “that wife pussy.” This one could be viewed as a spiritual sequel to “Like a Boss,” because both songs expertly apply hip-hop boasts to mundane, everyday activities.

8. “Spring Break Anthem”

One of the most immediately catchy songs in the Lonely Island catalog (and that’s saying something), this one was an amusing inversion of frat bro culture, as spring breakers mix “jokes about roofies” with plans of marrying another man. There are a lot of great lines in this song, and by the time they get to “nailing sluts and writing our vows,” it’s hard not to be in stitches. It also helped that this was the perfect inversion of just about every spring break-themed music video you’ve ever seen.

7. “Jack Sparrow” featuring Michael Bolton

As anyone who’s seen Office Space knows, Michael Bolton has been a punchline for years. Here, he gets in on the joke in a brilliant way, as we find out that Bolton is quite the film buff. The best part? When he recites one of the most memorable — and vulgar — lines from Scarface. Bolton did start his career as a metal singer, and this one showed he still had some edge left in him.

6. “We’re Back”

With The Lonely Island about to release their second album, they had to come out with something strong, so…they rapped about all the problems they have with their penises. Seriously. This one works mainly because of the aggressive delivery of each line, and the misdirection that you think the next person rapping might talk about something other than their junk, but they never do. Simple, but perfectly executed.

5. “Finest Girl (Bin Laden Song)”

This track from Popstar debuted recently on SNL, and proved that The Lonely Island are as creative and ridiculous as ever. This song basically plays on the ridiculous things people often say during sex — a girl tells Connor4Real that she wants him to “f*** her like we f****** Bin Laden,” and the rest of the song explores how silly that sounds when you really think about it. What really makes it work, though, is when the girl actually dresses up like Bin Laden, taking the metaphor to its logical conclusion.

4. “I Threw It on the Ground”

In this classic, our hero wants to rage against the machine, but feels a bit directionless, as his rants against “the system” are all fairly trivial. What really makes this one is Sandberg’s delivery. You can’t help but crack up at “Happy birthday to THE GROUND!” Of course, the directionless anger of this one reminds us of another clueless Andy Samberg character….

3. “Ras Trent”

In which insufferable rich white college kids who just discovered reggae get their comeuppance. The video makes this one even funnier because of Samberg constantly smelling his dreads. Throughout the song, patois expressions are randomly inserted into the lyrics (“Excuse I!”), and it becomes clear that Ras Trent has no clue what he’s singing about. This was a great way of taking on the rich-white-kids-with-dreads phenomenon without coming off as too preachy.

2. “Lazy Sunday”

The song that started it all. When this sketch aired in December 2005, SNL was receiving some of its worst reviews in years, and was stuck in an awkward transitional period. Then, “Lazy Sunday” blew everyone’s minds. It was the first Lonely Island track on SNL, and it went a long way in establishing YouTube. One of the most important SNL sketches of all-time, and one of The Lonely Island’s very best.

1. “Dick in a Box”

The first Timberlake collaboration was easily the best, as ’90s R&B/New Jack Swing is mocked brilliantly here. It’s hard to say what works best about this one; when they give instructions? Samberg and Timberlake’s ridiculous outfits? Really, the whole thing is just perfect from start to finish, and despite some extremely stiff competition, it ultimately ranks as their finest work.