Odds are, you have heard of The Lonely Island, the musical comedy group consisting of Andy Samberg, Jorma Taccone, and Akiva Schaffer, from Saturday Night Live or their films Hot Rod (2007) and Popstar: Never Stop Never Stopping(2016). We all have a favorite song or era of theirs, and although there are way too many songs to choose from, here are 34 of The Lonely Island's best works to date.
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"Lazy Sunday"
NBC
Let's take it back to 2005! The literal second Saturday Night Live digital short after "Lettuce," which is also incredible if you haven't seen it. I'm pretty sure "Lazy Sunday" was one of the first viral YouTube videos, and it only took seven years for Andy Samberg and Chris Parnell to reunite and give us a sequel!
2 of 34
"Natalie's Rap"
NBC
You know the one. SNL alum Chris Parnell sits down with actress and Harvard graduate Natalie Portman, who turns out isn't as good as she may seem. We love Andy in the random Viking gear, too. Watch the sequel from 2018, "Natalie's Rap 2," here.
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"D—k in a Box"
NBC
Ah yes, the iconic "D—k in a Box" video! This Christmas-themed, '90s-inspired R&B ballad was all anyone talked about in 2006. Thankfully, this wasn't the last time we got to see Justin Timberlake and Andy Samberg as these characters.
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"Iran So Far"
NBC
A love song for then-Iranian President Mahmoud Ahmadinejad, this digital short was delightfully weird. Maroon 5's frontman, Adam Levine, was a real team player, which made for an excellent chorus and harmonies with Samberg. And yes, it was inspired by A Flock of Seagulls' 1982 song, "I Ran (So Far Away)."
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"Space Olympics"
NBC
The grip this song had on me in 2008! If there's one thing that is true about digital shorts, it is that they don't have to make any sense at all. When I am gone, I will have high expectations for the year 3022 and the "Space Olympics" that will hopefully take place.
6 of 34
"Ras Trent"
NBC
Another sketch of Andy just being Andy, and we loved it. It is safe to say that The Lonely Island's first album, Incredibad (2009), was always playing on repeat and that I knew (and still know) every single word to "Ras Trent." Rastafarianism, am I right?
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"J—z in my Pants"
NBC
I won't lie; this sketch corrupted my innocent little brain, but it was just too funny! What can I say? Comedy rap is my jam. Always a good go-to for karaoke, if you ask me!
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"I'm On a Boat"
NBC
"I'm On a Boat" is another karaoke gem that absolutely kills! Everyone was obsessed with this period of The Lonely Island and couldn't get enough. T-Pain crushes it, and we wouldn't expect anything less.
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"Like A Boss"
NBC
Seth Rogen was featured in the digital short that aired in 2009, and if you look closely, you'll see a baby John Mulaney getting micromanaged by "the boss," Andy Samberg. Favorite lyric: "'So that's an average day for you then?' 'No doubt.'"
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"Motherlover"
NBC
Justin Timberlake and Andy Samberg return, supposedly five months after "D—k in a Box," to show the other's mother a good Mother's Day. "Motherlover" was evidently supposed to be released on The Lonely Island's first album but ended up being the fourth single on their second, Turtleneck & Chain (2011).
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"Threw It on the Ground"
NBC
Stick it to the man and throw anything and everything on the ground! My friends and I thought this short was the funniest thing, and, you know, we weren't wrong.
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"Boombox"
NBC
While I don't remember "Boombox" leaving a strong impression on me in 2010, the beats and featured artist, Julian Casablancas, make this song worthy of the "best of" list. Plus, the music video is awesome.
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"Sax Man"
The Lonely Island
I wish this song had a music video so badly. Jack Black makes any song better, and while The Lonely Island's voices aren't present in the track, "Sax Man" is one of the best on the album.
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"We Like Sportz"
The Lonely Island
A sequel to the song "Just 2 Guyz" from 2005, "We Like Sportz" keeps the party between "Guy #1" (Akiva Schaffer) and "Guy #2" (Jorma Taccone) going. This time the guys talk sports while ensuring that loud-mouth Steve (Andy Samberg) doesn't ruin their fun.
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"Great Day"
NBC
"Great Day" is amazingly chaotic, with Samberg's character Dennis (clearly addicted to cocaine) singing faster as his day gets wilder. Although it didn't make the album, it is featured on the Turtleneck & Chain DVD.
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"Shy Ronnie 2: Ronnie & Clyde"
NBC
Almost a year after the first "Shy Ronnie" digital short, Rihanna reunites with Shy Ronnie (Samberg) to rob a bank a la Bonnie and Clyde style. The two songs deserved a spot on the album, but hey, there's always YouTube.
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"I Just Had Sex"
NBC
"I Just Had Sex" featuring Akon was the first single off of Turtleneck & Chain. Yet another song with a hilarious music video, this short has everything: Jessica Alba, Blake Lively, and a cameo by John McEnroe for some reason.
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"The Creep"
NBC
"The Creep" featured Nicki Minaj and John Waters and was one of the more entertaining shorts to grace our televisions (as well as the internet) in the 2010s. This song had everyone wanting to "do 'The Creep.'"
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"Jack Sparrow"
NBC
"Jack Sparrow" was, in one word, interesting. I still have so many questions as to how this song came to be, but it doesn't matter. Michael Bolton did promise us a sexy hook, after all, and we dug it.
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"3-Way (The Golden Rule)"
NBC
Starting as a continuation of "Motherlover" with cameos by Susan Sarandon and Patricia Clarkson as Justin and Andy's moms, "3-Way (The Golden Rule)" features Lady Gaga, the two's new love interest. The song was initially released as a standalone single but is also on the group's third album, The Wack Album (2013).
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"Turtleneck & Chain"
The Lonely Island
The album of the same name is obviously awesome, but the song featuring Snoop Dogg is something else. It makes for a great Halloween costume and begs the question: Who can't they get on a song?
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"YOLO"
NBC
Adam Levine is back again with The Lonely Island, this time with Kendrick Lamar! "YOLO" goes for the opposite effect of "You Only Live Once," where instead of living life to the fullest, the group is extremely paranoid and does everything to stay safe, including pulling out all their teeth so they don't bite their tongues.
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"Hugs"
NBC
I somehow missed "Hugs" when Andy Samberg hosted the SNL season 39 finale in 2014. I want to say that I eventually saw the video at some point before now but do not remember; however, it definitely belongs on the list. Pharrell can do no wrong, and this song is all the more evidence. The video also features Tatiana Maslany and Maya Rudolph as Oprah.
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"Spring Break Anthem"
The Lonely Island
"Spring Break Anthem" is iconic. The song shows how ridiculous it is that same-sex marriage is perceived as absurd while typical spring break behavior is deemed normal. The video features Zach Galifianakis, Edward Norton, and James Franco as the group's soon-to-be husbands.
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"Go Kindergarten"
The Lonely Island
Again, it's hard to keep up with The Lonely Island after their departure from SNL, but I try. "Go Kindergarten" with Robyn, Sean Combs, and Paul Rudd is severely underrated! If you see these guys in the club, I would do whatever they say if I were you.
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"Finest Girl (Bin Laden Song)"
The Lonely Island
The Popstar: Never Stop Never Stopping era was a force to be reckoned with. If I told you I was shocked by the lyrics of "Finest Girl (Bin Laden Song)," I would be lying. Do we remember "Iran So Far?"
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"I'm So Humble"
The Lonely Island
Adam Levine hologram: check. "I'm So Humble" was the moment straight out of the gate. This movie was incredible and smart as hell, intercut with celebrity interviews, including Mariah Carey, who can relate because she's the most humble person she knows.
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"Mona Lisa"
The Lonely Island
You know what? Conner4Real (Samberg) was right: the Mona Lisa is overrated, and I'm glad he wrote a song about it. His stage performance, complete with the backup dancers, was perfection. I want this tour to happen for real.
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"Equal Rights"
The Lonely Island
"Equal Rights" with Pink is amazing. It might not have directly attacked Macklemore's 2012 song "Same Love," but The Lonely Island freaking dropped the mic on this one. The best line during the scene in the movie has to be, "He's writing a song for gay marriage like it's not allowed. It's allowed now."
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"Turn Up The Beef"
The Lonely Island
"Turn Up The Beef," with Emma Stone, otherwise known as the "catchphrase verse," is a low-key banger, that is, until Conner4Real gets ahold of it. As for the best catchphrase, it's a tie between "Sorry, Dad" and "PATRICK STEWART MONEY."
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"Karate Guy"
The Lonely Island
I feel like "Karate Guy" is a bit underrated. The "Style Boyz" can do no wrong, whether doing the "Donkey Roll" together or just kicking it — like hanging out, not kicking something with their feet. Honorable mention: "Sick Glenda," the song they revisit toward the movie's end.
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"Things in My Jeep"
The Lonely Island
Akiva Schaffer's character Lawrence's (AKA "Kid Brain") one song featuring Linkin Park was a masterpiece. As someone who owned a Jeep at the time, "Things in My Jeep" doesn't get nearly enough credit for just how great it is, despite having different things in my Jeep.
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"Incredible Thoughts"
The Lonely Island
Finally, the Style Boyz are officially back together and here to share their "Incredible Thoughts!" Just having Michael Bolton and Justin Timberlake in the same song was awesome, especially since Timberlake was Conner's personal chef in a fish costume. We also appreciated his manager, Harry (Tim Meadows), playing the sax and Usher doing the "Donkey Roll" toward the end.
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"IHOP Parking Lot"
Netflix
I could've ended it there, but we can't forget about the Netflix special, The Unauthorized Bash Brothers Experience, from 2019, with Andy and Akiva as MLB players, Jose Canseco and Mark McGwire. Their fictional rap album from the '80s featured many artists and actors like Sterling K. Brown as Sia, but the best song is arguably "IHOP Parking Lot" with Haim and Maya Rudolph, where they repeatedly tell Jose and Mark to shake their nasty butts.
Shelby Weimer is a content creator and comedy writer based in Brooklyn, New York, who grew up watching and quoting way too many movies, inevitably leading her to earn a film degree (oh no) with a focus on screenwriting. She is well-versed in the world of TV and film production, having worked in just about every role in the entertainment industry, from background actor to producer. Shelby has written for various online publications, including Screen Rant and Vocal Media, but more importantly, her writing was featured onTikTok by comedian Matt Braunger. When she isn’t loving on her cat or working on scripts and sketch ideas, she’s most likely listening to her music a little too loud or watching Love Island. Both? In the words of Tulio and Miguel from the extremely underrated DreamWorks animated film The Road to El Dorado, “Both is good.”