The 10 Best Lonely Island Songs by Austin Shinn

Comedy music is one of the hardest things there is. As has been noted by other reviewers, you have to be extremely good at two things that are extremely hard. You have to be very funny and have good music or nobody will listen to you. You might get one or the other but usually neither.

Well today we’re looking at a group that’s the prime example of what this should be. Yeah I’m really expressing a hot take to say The Lonely Island is great at comedy music. This has been an established belief since at least 2006 but it keeps being true. So why not celebrate something really awesome. There’s a lot to study here.

10. “Finest Girl.” Warning: There is a lot from the Popstar soundtrack and that’s how it should be. A movie should be the grand statement for a comedian and they had one hell of a statement here. I suspect putting this at 10 is a slightly controversial step since this usually ranks higher but it’s only down here because I prefer 9 other songs. Trust me, this is a hell of a track. Musically it’s a wildly complex work while it’s one long weird as hell study of a very irregular sexual encounter. Just…best listened to.

9. “Go Kindergarten.” So simple but so great. The perfect example of a band that was a needed voice of parody in the LMFAO/Black Eyed Peas/Pitbull era. Just a random series of commands but they’re hysterical. Robyn is an inspired guest, a pop artist who kept doing what she was doing in 1997 and wound up sounding avant garde in 2010.

8. “Mona Lisa.” Why this one? It’s an absurd concept, a diss track to a painting. But of course the core joke of the song is how people think they’re above things like classic art and architectural marvels and really how ludicrous that sounds. It’s lacerating satire of a mindset that deserves it. Underrated musically too. As a bouncy pop song, it’s an endless toetapper.

7. “F*** Off.” I’m probably putting this one lower than I think it belongs. Musically it’s imitating unimpressive songs so it’s ok that it’s just OK. But what a marvel of profanity this is. Not just the filthiest song they’ve recorded but up there in the pantheon of great obscenity.  The joke that it’s this raunchy scream at parents played as a cute song of rebellion is glorious. So crude and so great.

6. “3 Way” Whittling the Timberlake collaborations was hard. I think a case can be made for all 3 on this list. Dick in a Box succeeded as a weird rough first try. Motherlover is just a weird win. But this one has so much going for it. The music is great. The lyrics are strong. Lady Gaga is always a plus. But what puts it over is the beauty of the message. The group has always had a refreshingly chill stance with songs like No Homo and Equal Rights mocking homophobia and gay panic. The song is about a “devil’s threesome” and they treat it as “hey you’re my best friend so why the hell not, it’s y’all that are whiny.” Sure it’s still juvenile but it’s just a funny track.

5. “I Threw it on the Ground.” Couldn’t have this outside the top 5. There are definitely tracks that lean more on the comedy to get the song to a success and this is one. It just happens to have a great joke to do so with. A rebellious iconoclast increasingly reveals how he’s less a free thinker and more an asshole. It’s funny because we all know this person. It’s a true song. And it stays in your head.

4. “I’m So Humble.” Putting this above any of the other songs on the Popstar soundtrack was hard. But this is something exceptional. I put a lot of it down to that sample, which is the song Heartaches by the Marcels. That doo wop sample is so tight that the whole song has to be bound to that level. Andy Samberg has never had a more convincing pop singer flow as he does, firing every crazy line at rapid fire. Then there’s Adam Levine who seems content to phone it in except in collaborating with them. Levine is actually really great here. This was how the film started and it was the right way of assuring us they had nothing to be humble about.

3. “I’m on a Boat.” This was I feel the moment that they established they meant the music thing. While we’d had the Timberlake collaboration, that could be written off as part of SNL. Here they brought in T-Pain, who at that moment was huge on the very kind of song this riffs on, and showed they were going to play on this level. It’s a brag rap song except about the bland subject of taking a trip on a boat. But the song transcends the “haha white guys” level to become a legitimately great anthem for partying.

2. “YOLO.” The closest the band has come to a standard parody song. This takes the idea of Drake’s The Motto and twists it to become a song about deranged paranoia. Every line of this is well crafted and it escalates into a fever dream of terror. Then you’ve got Kendrick Lamar and Adam Levine, both of whom never once betray the joke. They sound like they’re just doing their usual thing. Everything about this song works.

Honorable mentions:

“Legalize It.” The group destroys white fixation on weed culture gloriously while also giving the indication much indica was consumed making this.

“Japan.” One long joke but a great one.

“Spring Break Anthem.” The way this song contrasts the crude ugliness of spring break with the joy of gay marriage rules.

“Spell it Out.” Another joke but an artful one.

“Jizz in My Pants.” Damn but the hooks on this…

  1. “Jack Sparrow.” It’s all down to what they do with Michael Bolton. A hack comic would make the repeated joke that Bolton is a terrible performer who should be laughed at. But…he’s obviously not. He’s got a god tier voice and he uses it in full force here. No the thing that makes this their best is the out of nowhere joke about Bolton singing about movies as the hook. That’s weird and funny and with Bolton seriously firing on all cylinders, it’s endlessly listenable. It hardly hurts that the song is just a killer club song in an era with a ton of those. The beat is great. Their flow is strong. This is a classic.

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