Here we are. We made it. We’ve scaled the mountain, and only the best songs from The Lonely Island remain. I hope you’re proud of yourself for completing this journey with me. I know I’m proud of you. I’m sure Andy Samberg, Akiva Schaffer, and Jorma Taccone are proud of us too.
I’ll keep the rules recap short since I’m sure you know the drill by now. I’m taking the songs that are left and ranking them based on the quality of both the jokes and the music. Music videos when present also factor into the rankings.
At this point, there are no bad songs left. There are barely any good ones left. What we have now are the greatest songs in The Lonely Island’s catalogue. We’re starting at 26 today, and we’re not stopping until we reach number 1. This is the moment we’ve been building towards our whole lives. Let’s begin.
26. Donkey Roll: Popstar
The extremely catchy Style Boyz song that launched the group into fame before the events of the movie. The dance that goes with it is excellent, and if Usher is on board with it, so am I.
25. Turtleneck & Chain (ft. Snoop Dogg): Turtleneck & Chain
Our ranking today begins with the title track from the group’s sophomore album. Like “Punch You In The Jeans,” there are a bunch of great clothing-based verses, plus Snoop Dogg is here this time and throws down a vintage Snoop verse. I relate to all the references to light beer because I am poor and also have garbage taste in alcohol.
24. Who Said We’re Wack?: Incredibad
This song is up this far partially for historic reasons. This is the first track on The Lonely Island’s first album. That’s important! It’s also a short and to-the-point fun little track about the devastation of being called “wack.” That’s no small deal.
23. Space Olympics: Incredibad
At this point, it would probably be better to host the Olympics in space than anywhere here on Earth. This song perfectly captures both the futuristic techno sounds of what I imagine space music to sound like and the utter impossibility of smoothly running the Olympics. The video is fantastic as well. Samberg screaming “You’re in the motherfucking Space Olympics!” into Michael Phelps’s ear will never not be funny.
22. Maximus: Popstar
In Popstar: Never Stop Never Stopping, Maximus is Conner4Real’s pet turtle, a companion he’s had since childhood. This is an ode to a pet turtle. It’s also a fantastic riff on Bon Iver’s general sound, so much so that it could stand on its own as a Bon Iver song.
21. Semicolon (ft. Solange): The Wack Album
Semicolons are no fun. The Lonely Island knows this, so they made a whole song about it. Solange on the hook is killer, and I wish she was my English teacher in high school. The group always employs impressive wordplay, but this track might be the greatest testament to their skills in that category.
20. We Need Love: The Wack Album
The return of Guy #1 and Guy #2! Instead of sports, this time the two are turning their attention to romance. The creepy advances and boasts work even better with the delivery and the poorly edited music video. The two still have time to diss their friend, Steve, though. Steve has it rough.
19. Dramatic Intro: The Wack Album
The group’s best intro track on one of their albums. In a parody of the heroic montage, this starts off simply enough with audio of the group winning awards as a lovely piano track plays. Things start to escalate into the outrageous, eventually ending with the group being beaten to death with their own dicks. It’s a tough way to go, but this track exemplifies The Lonely Island’s use of hyperbole in order to land a joke.
18. Mona Lisa: Popstar
We all have the experience of witnessing a critically-acclaimed movie, song, book, or other art form and having it not speak to us as it does to others. It happens! Everyone’s tastes are different. This is that feeling (except in song form and about the most famous painting in human history). The lengths Conner goes to in order to trash the painting are both appalling and make for a fantastic song.
17. Hugs (ft. Pharrell): The Wack Album
A song about hugs as one night stands. Also a parody of the pervasive attitude in music of viewing women as disposable objects. I never knew there were so many ways to describe hugs, and the drumline-inspired instrumental is top notch. The Wilt Chamberlin line speaks to me as a sports fan, and Pharrell is just plain disrespectful here. Hugging your mom while he wears your dad’s PJs? Ice cold.
16. Ibitha: Popstar
Another highly offensive smash from Conner. It’s an entire track about the Spanish accent he experienced while in Ibiza, transformed here into “Ibitha.” It’s one of a string of tone-deaf tracks that sinks him in the movie, but it is a dance track to end all dance tracks. The recipe for paella in the middle sounds like something I would like to eat.
15. After Party (ft. Santigold): Turtleneck & Chain
The concept of an after party is an alluring one in entertainment. You often hear the after party is better than the main party. But what if the after party involved a full on existential crisis and an excessive amount of jerking off? Honestly, this song is so high because Santigold is amazing and turns anything she touches into gold.
14. 3-Way (The Golden Rule) (ft. Lady Gaga and Justin Timberlake): The Wack Album
The third song of the trilogy of Samberg and Timberlake. Even more references to bad ’90s R&B, including excessive use of the word “yeah,” hideously outdated references, and even more hideous neon outfits. It does do well in capturing the wonderful sounds of ’90s R&B. While I get what the song is going for in the absurdity of there being a “rule” about what is and isn’t gay when participating in sex with multiple partners of differing genders, it doesn’t do it quite well enough to elevate it over spot 15. It also criminally underuses Lady Gaga, who is brilliant with what she’s given. I am also still immature enough to laugh at “helicopter dick.”
13. I’m So Humble (ft. Adam Levine): Popstar
The joke here is that Conner4real is not humble at all. It’s not subtle or particularly clever. The song itself more than makes up for it. The vocal sample is amazing, the lyrics are fun and engaging, and you know my feelings on Adam Levine (he’s great). This song is going on my main summer playlist, and you can’t stop me.
12. The Creep (ft. Nicki Minaj and John Waters): Turtleneck & Chain
We all know an extra creepy dude. This is an entire dance based around the concept of that creepy dude. The synths lurch and leap along in a suitably unsettling fashion, and the slicked back hair and pencil mustaches make the video shine. It’s a testament to Nicki Minaj’s rapping ability that she can deliver a world class verse about watching people undress in a locker room. Is there anything she can’t do? Finally, John Waters is a perfect choice for the opening and closing narration.
11. Ashley Wednesday (ft. Seal): Popstar
Musically, this is a slowed-down, softer version of “Mona Lisa,” so you know it sounds good. It’s also surprisingly touching for a Lonely Island song. Conner has Seal perform this for the titular Wednesday (played by the incredible Imogen Poots) when he proposes to her. Yes, he proposes as a way to flip the news cycle, but still! There are still jokes in the track (shots at France), but Seal imbues this with enough tenderness and earnestness to make it shine. Maybe I’m just a sap that gets emotional in movies, or maybe this song is actually beautiful. Maybe it’s both.
10. Boombox (ft. Julian Casablancas): Incredibad
A techno track that expertly builds musical tension through its verses in order to really sell the chorus. Julian Casablancas brings his trademark croon and Strokes sensibilities to push it to a new level. The video contains fantastic outfits and A+ harmonious dancing. The boiled goose gag is hilarious, and we all need a cautionary tale about the power of a boombox.
9. Incredible Thoughts (ft. Michael Bolton and Justin Timberlake): Popstar
The climactic finish to Popstar. The Style Boyz reunite and enlist Lonely Island mainstay guests Michael Bolton and Justin Timberlake (as Mr. Fish) to bring it home. How incredible these thoughts are is questionable, but they’re delivered with such a straight face from the group that it works. And think what you want about him, but Bolton still has a fantastic voice that grants weight to the track.
8. Ras Trent: Incredibad
We all know a Trent. The guy who loves Bob Marley even though he doesn’t know anything about Marley’s philosophy beyond smoking weed. The song is some reggae goodness even as it takes down those who know nothing about Rastafarianism. It’s scary how accurate Samberg is here: smelly white people dreads, bongs made out of soda cans, naming random Jamaican things, and the perfect moment where he mumbles while he walks in front of some real Rastafarians. Listen and laugh at Ras Trent, don’t be Ras Trent.
7. Jack Sparrow (ft. Michael Bolton): Turtleneck & Chain
Fun story: when this song came out, there were only three Pirates of The Caribbean movies out, with the fourth a few weeks away. Simpler times. Once again, Bolton absolutely nails his part, both the vocal ability and the fascination with movies. As someone else who loves movies, this song speaks to my soul. It’s a great club track in its own right, and I love how Bolton goes so off course with movies he eventually comes all the way around to a movie that works for the track in Scarface. Those outfits in the video are pretty spectacular as well.
6. Threw It On The Ground: Turtleneck & Chain
Fantastic anti-establishment, spoken-word art parody right here. The song is good, but the video puts this firmly over the top. The outfit, the slow-motion shots of Samberg throwing things on the ground, and Elijah Wood and Ryan Reynolds tazing Samberg’s butthole are all brilliant. The Jenny Slate bit with the cellphone is amazing. You just can’t trust the system, man.
5. Finest Girl (Bin Laden Song): Popstar
The weird, unusual, appalling gem of Popstar. What brings this song a long way is Conner constantly acknowledging how bizarre a request like “getting fucked like Osama Bin Laden” really is. The facial expressions he makes in the music video as this girl (played by SNL’s Vanessa Bayer) details her requests are priceless, as is his willingness to go along with it. “Seal Team 69” is iconic. Each lyric is well thought out and perfectly delivered, and I love the dumb joke at the end of the video. Also, there are quite a few flattering shots of Samberg’s ass.
4. Motherlover (ft. Justin Timberlake): Turtleneck & Chain
It’s off-putting in the best possible way and is the best song of the three Samberg and Timberlake did together. The verses have that nice driving beat behind them, and the chorus is big and jubilant. This might be the best example of The Lonely Island’s ability to take a bizarre concept and just run with it. Didn’t get a gift for your mom for Mother’s Day? Of course, you’ll let your best friend sleep with her as her gift. Patricia Clarkson and Susan Sarandon also do good work as the duo’s mothers in the video.
3. Lazy Sunday (ft. Chris Parnell): Incredibad
The beginning of all of this. Without “Lazy Sunday,” this list doesn’t exist. It was the world’s first major taste of the group’s musical and comedic talent, and it helped turn Andy Samberg into a comedy megastar. This isn’t just a legacy pick, though. This song is fantastic. The narration of a lazy day is instantly relatable, while the lyrics written are still clever and hilarious. The musical breakdowns are stuff of comedy legend now while still sounding great, and there’s something to be said for mild-mannered Chris Parnell rapping like his life depends on it. Truly a modern comedic masterpiece and milestone.
2. YOLO (ft. Adam Levine and Kendrick Lamar): The Wack Album
This song is a distillation of everything that makes The Lonely Island great. Is the song good? Yes, I’m convinced this would be a radio smash in any sense of the word if the group wanted it to be. A good and worthy target? Yup, the YOLO craze (thanks, Drake!) of a few years ago was always a perfect target for parody. A great video? Yes, watching the group give detailed instructions on how to completely danger-proof your life is funny as hell. Good guest spots? You know it. Adam Levine crafts an impeccable hook, and Kendrick “best rapper of our generation” Lamar lays down the best and most interesting verse about personal finances you’re ever going to hear. “YOLO” might be The Lonely Island at their purest, and its wonderful.
1. I’m On A Boat (ft. T-Pain): Incredibad
I thought long and hard between “I’m On A Boat” and “YOLO” for the top two spots. I’ve switched them back and forth a few times, knowing that “YOLO” at number one would be a huge upset and a scalding hot take. I love “YOLO.” But I love “I’m On A Boat” more. All of the criteria I just listed above apply here. There’s the thrill of something so mundane as being on a boat. The group’s bombastic and over-the-top delivery in the lyrics is a delight. T-Pain is here at the height of his popularity and powers. The video is superbly silly, a play on a trend in hip-hop videos where they always had to have a boat. And with a tie in virtually all the categories I’ve been judging by, “I’m On A Boat”‘s significance wins out. This is the Lonely Island song. “Lazy Sunday” was the beginning, but “I’m On A Boat” was the ascension. It was inescapable. It got nominated for a Grammy in a major category. If we’re ranking Lonely Island songs (which we are), there’s no way that “I’m On A Boat” is anything but number 1.
We’ve reached the end. We’re at the top. Now take this knowledge you have earned and go forth boldly into the future. This knowledge will serve you well. I now bid you adieu and rest my case. And remember: You Oughta Look Out.