You didn’t think we’d leave you wanting for more, did you? As promised, the show must go on. This is Part 2 of the ranking of every single song from The Lonely Island, comedy group of Andy Samberg, Akiva Schaffer and Jorma Taccone. On Tuesday we began this journey, and today we’re going to bring you within sight of the finish line.
Let’s do a quick refresh on the rules: all 81 songs from the band’s four albums are what we’re working with. A song will be judged on what the joke is, how effectively said joke is delivered and how funny it ends up being, how good the song itself is, and finally both good and bad aspects from the music video, if there is one.
Today, we’ll start by counting down from song 53 all the way to song 27. At this point, these are all songs that are good to some degree, meaning the choices are starting to get tough. Strap in, we’re on our way.
53. Rock Roll Skate: Popstar
A lot of Popstar‘s music revels in audacity in order to make the point. This is one of those, except there’s not much of a point and it’s just there. It’s not terrible, it’s not great, it’s there.
52. Hunter The Hungry Is Gon’ Eat: Popstar
In Popstar: Never Stop Never Stopping, Hunter The Hungry (played by Chris Redd) is a rapper brought onto Conner4Real’s tour by management to prop up ticket sales. He is clearly modeled after Tyler, The Creator. Therefore, your opinions on Hunter will almost entirely depend on your feelings about Tyler. The hook to this song absolutely bangs, though.
51. I Don’t Give A Honk: The Wack Album
In a sea of cursing, it’s surprisingly funny to hear the trio avoid any form of curse word for an entire song. Plus, “honk” is a fun word to rhyme with other words.
50. Santana DVX (ft. E-40): Incredibad
There are a million celebrity endorsements out there. Would it really be that unusual if guitar legend Santana made an alcoholic beverage? There’s a great reference to that Rob Thomas song we all love and cherish, plus E-40 crushes his verse as Santana.
49. Me Likey Dat: Popstar
A Style Boyz track from the movie. If this song were longer than a minute, it would be higher up the rankings because the ’90s boy band vibes are strong with this one.
48. Rocky: Turtleneck & Chain
This is a play on the weird trend in the ’90s started by Aaron Carter’s “That’s How I Beat Shaq” about interacting with famous athletes. In this case, Samberg tells the tale of fighting famed, fictional boxer Rocky. It doesn’t go well for Samberg.
47. Go Kindergarten (ft. Robyn): The Wack Album
I have to admit, I don’t love this song. I get what they’re going for with sending-up dance tracks that contain instructions, but in practice, it’s just a lot of shouting. What saves this song is the presence of Robyn, who rules, and the music video, which delivers the Sean Combs/Paul Rudd buddy flick I never knew I needed.
46. Perfect Saturday: The Wack Album
The prequel/sequel to Lazy Sunday. Except instead of cupcakes and whimsical fantasy movies, it’s the instrumental that’s whimsical, and it’s about a disgusting friend crashing at your place. We all know a Ned like in this song. You know who you are.
45. Mama: Turtleneck & Chain
This list missed Mother’s Day by a decent clip, but this song is a track dedicated to mothers. And to the fury of children when mothers interrupt recording/playing video games/doing whatever. Being a parent seems hard. I’m glad I’m never gonna do that.
44. Japan: Turtleneck & Chain
It’s an ingenious ploy. Make a song about Japan so the label will have to pay for the music video to send you out there. Sadly, this track never got an actual music video, which I bet would have been hilarious.
43. Jizz In My Pants: Incredibad
Premature ejaculation is funny! This is one in a string of releases from Incredibad that pushed The Lonely Island into the internet kings they are today. It’s not that it’s bad, it’s just that it’s not as good as some of the titans we have coming up higher on this list. This is exactly how I felt when I first saw The Sixth Sense, though.
42. Spring Break Anthem: The Wack Album
This is another song in the spirt of “No Homo” that uses toxic hyper-masculinity to combat homophobia. On the surface, it’s an ode to all the frat bros that you see on the beaches during spring break. It’s also about two men getting married. The video is the most star-studded affair yet on these rankings, with Zach Galifianakis, James Franco, and Edward Norton serving as the lucky men marrying the members of The Lonely Island.
41. We Like Sportz: Incredibad
This is the first album appearance of Guy #1 (Schaffer) and Guy #2 (Taccone) as “Just 2 Guyz.” As the title implies, they are just two(2) guys(z). Here, they sing about their love of all sports activities. The monotone delivery makes this series, as does the constant insults hurled toward their friend, Steve. I feel bad for Steve.
40. Shy Ronnie 2: Ronnie & Clyde (ft. Rihanna): Turtleneck & Chain
First off, Rihanna is brilliant and queen of the universe and can do no wrong. This song is excellent. It sounds like it could be an actual radio hit. The bank robbery angle is brilliant. It’s spot on the rankings is hurt by two things. The first is my general dislike of the concept of Shy Ronnie to begin with. A rapper with stage-fright doesn’t do much for me. The second is the fact that this is the only Shy Ronnie track on an album, which hurts the overall understanding and delivery on it. Shoutout the surprise guest at the end of this video.
39. Hey Ya Ho (Hunter The Hungry): Popstar
There’s not much to say about this that wasn’t already said about “Hunter The Hungry Is Gon’ Eat,” but this is a better version of that song.
38. Karate Guy: Popstar
This is at number 38 because it might be the catchiest song on the list so far. It tops out at 38 because the only joke is that it’s generally dumb. There are catchier Lonely Island songs with better jokes out there. There are catchier songs with better jokes in Popstar.
37. 2 Banditos: Popstar
We’ve got a run of Popstar songs right now. This one is a collaboration between Conner and Hunter. The Red Hot Chili Peppers reference would have it high on this list even if it wasn’t a low key banger.
36. Sax Man (ft. Jack Black): Incredibad
The story of a baby who can play the saxophone. The instrumental is as funky as you would imagine for that story, and Jack Black lends his considerable comedic timing and vocal range to this one to make it a winner.
35. The Compliments (ft. Too $hort): The Wack Album
It’s just a bunch of guys complimenting each other, nothing weird about that. The mere presence of Too $hort is fantastic, even if he doesn’t have a whole bunch to do on this track.
34. Turn Up The Beef (ft. Emma Stone): Popstar
This is the infamous “Catchphrase Verse” from Popstar that, in the movie, launched Conner into stardom (although Lawrence wrote it and Conner refused to give him credit). The verse is hilariously nonsensical, as it’s made up entirely of potential catchphrases. Emma Stone is great, as well. As far as I’m concerned, this is the prequel to La La Land.
33. Dick In A Box: Incredibad
If I’m gonna get blowback on these rankings, I have a feeling it will start here. The first of the Justin Timberlake/Andy Samberg team-ups is also the weakest. That’s not saying its bad, its still absolutely hilarious. The embodiment of bad ’90s R&B, the duo of Samberg and Timberlake is truly a force to be reckoned with. It’s just done better in later songs. (NOTE: the video has been scrubbed from Youtube for some reason, which is why the NBC censored embed is being used here.)
32. Equal Rights (ft. P!nk): Popstar
This is as close as The Lonely Island comes to ever calling out a specific person. This is the first single from Conner’s failed second album, ConnQuest, and it has a political message for the world. That message is that Conner supports equal marriage rights. But Conner makes it very clear that he himself is not gay, repeating “not gay” throughout the song and naming other typically masculine things like “sports” and “hot wings.” This is pretty clearly a jab at Macklemore and “Same Love,” which received some criticism in real life for having a straight artist leading the charge on LGBTQ issues. I believe those criticisms are valid and “Equal Rights” makes a good point here. I also believe Lonely Island is better when addressing an issue at large instead of focusing on one specific person.
31. I Run NY (ft. Billie Joe Armstrong): The Wack Album
Told from the perspective of the Mayor of New York, it turns out running a city is hard. And not just running it from a musical standpoint. Literally making everything work. Billy Joe Armstrong really steals the show here, along with the reveal that there are giant mutant rats that must be fought in the sewers. I think we all knew those existed, though.
30. Should I Move? (ft. Akon): Popstar
Sometimes figuring out what to do with your real estate dealings can be hard. Thankfully when you’re rich, and also Akon, you can afford to mull it over a bit. Speaking of Akon…
29. I Just Had Sex (ft. Akon): Turtleneck & Chain
An ode to making love. The gleeful giddiness of Samberg and Taccone really sells this one. Imagining Akon with the same geeky excitement of a teenage boy over sex is also hilarious. The hook here is killer, and Jessica Alba and Blake Lively really help sell the video. Plus who doesn’t love an entire crowd of people in Times Square singing about doing it?
28. Fuck Off: Popstar
The trend of pop stars telling kids to be themselves and rebel against authority taken to its logical extreme. It’s so happy and celebratory in its own vulgarity and brazenness that its hard not to enjoy it. And I think we can all relate to wanting to tell a teacher or other agent of “the man” to fuck off. This song scratches that itch in the poppiest way possible.
27. You’ve Got The Look (ft. Kristin Wiig & Hugh Jackman): The Wack Album
Did watching Logan make you too sad? Want a way to make it less sad? Listen to this song at regular intervals throughout, as Hugh Jackman teams up with The Lonely Island to ponder if the woman heading out on the town with one of her boobs out is doing it as a fashion statement or just a wardrobe malfunction. You will never be able to look at Jackman the same way again after you hear him sing the phrase “one sassy titty.” Kristin Wiig comes in at the end to prove that it does not work both ways, as balls are definitely weirder than boobs. This is truth.
This has been Part 2 of our Lonely Island Rankings. Tune in at the end of the week to see which songs end up on top!