Top 20 Best Lonely Island Songs

Top-20-Best-Lonely-Island-Songs

Welcome to WatchMojo, and today we’re counting down our picks for the funniest, most memorable songs by the legendary trio that is Andy Samberg, Akiva Schaffer, and Jorma Taccone.

#20: “Sushi Glory Hole”
“Saturday Night Live” (1975-)
Hear us out: this ridiculous 2024 jam is an instant classic. Following up on Lorne Michaels’ promise that “Saturday Night Live’s” 50th season would be chock-full of surprises that honored the show’s history, “Sushi Glory Hole” momentarily teleported fans back to the group’s heyday. A bona fide, old school “SNL Digital Short,” this instantly recognizable Lonely Island number finds Andy Samberg and Akiva Schaffer pitching Maya Rudolph, Kenan Thompson, and Bowen Yang an admittedly questionable culinary experience. While the group’s trademark absurdist style is in full effect, we can’t help but draw attention to Samberg and Schaffer’s admittedly impressive flows. If only they weren’t rapping about, y’know, a friggin’ sushi glory hole.

#19: “YOLO” (featuring Adam Levine & Kendrick Lamar)
“The Wack Album” (2013)
Judging by the comments on our last Lonely Island list, we really messed up by not including this cautionary anthem! Honestly, we can’t argue with that — a song that includes this many warnings against everyday occurrences really makes you think. This paranoid pop-rap jam speaks to the trio’s ability to satirize pop music with real bite (and that’s not just a reference to featured guest Adam Levine’s suggestion that listeners pull out all of their teeth). Be sure to look out for Kendrick Lamar’s verse, in which the Lonely Island found the funniest possible way to use the future Pulitzer Prize winner: instead of a typically dynamic verse about living it up, we get painfully mundane financial advice. Thanks, we guess?

#18: “The Creep” (featuring Nicki Minaj)
“Turtleneck & Chain” (2011)
This is another fan favorite according to our own comments section, and we can certainly see its slimy appeal. Released in January 2011, “The Creep” parodies dance trends in hip hop that were popular at the time by adding a John Waters-themed twist, down to the gray suits and pencil mustaches. Samberg, Schaffer, and Taccone almost make being a Peeping Tom sound cool! Much like “YOLO,” a big chunk of the fun comes from an extremely game Nicki Minaj’s legitimately great guest verse — she’s so well-matched with the Lonely Island that we’re surprised that they haven’t collaborated again since. Once again, the trio takes hip hop and runs with it. We’ve never been so hyped to be creeped out before.

#17: “Incredible Thoughts” (featuring Michael Bolton & “Mr. Fish”)
“Popstar: Never Stop Never Stopping” (2016)
The climactic scene of the Lonely Island’s 2016 pop music mockumentary “Popstar” features this profoundly intellectual track, the result of a legendary jam session between the reunited Style Boyz (played by the group’s members). In a scene that seemingly pays homage to the NSYNC reunion at the 2013 MTV Video Music Awards, Conner, Lawrence, and Owen unveil a brand-new song that reveals their machinations of their so-called “incredible minds.” The song is a hilariously ridiculous mashup of preposterous one-liners, all anchored by special guest Michael Bolton’s big, sexy hook. Wait a minute, who was under that fish costume?!

#16: “Oakland Nights” (featuring Sia)
“The Unauthorized Bash Brothers Experience” (2019)
If you’re a longtime Lonely Island or Oakland Athletics fan (or both!) and you haven’t seen “The Unauthorized Bash Brothers Experience,” get on it! If you know nothing about baseball, then you’ll probably be pretty lost, but at least you’ll have a good time. Paying tribute to the legendary careers of Jose Canseco and Mark McGwire (played by Samberg and Schaffer respectively), the two meatheads attempt to pick up two professional gals played by Jenny Slate and Hannah Simone. While their awkward attempts at romance may be dead in the water, we can at least be thankful for Sterling K. Brown’s all-in performance as Sia.

#15: “Equal Rights” (featuring P!nk)
“Popstar: Never Stop Never Stopping” (2016)
When even the featured artist appears to realize halfway through how absurd your song is, you may want to reevaluate things. In an apparent parody of Macklemore’s well-intentioned “Same Love,” Conner4real attempts to extend a hand to the LGBTQ+ community. However, gay marriage is now legal, so it’s not entirely clear as to why Conner thinks this is a problem that still needs to be addressed. Conner’s profound professional loss is our comedy gain: his efforts to be inclusive are quickly overshadowed by his obvious fear of appearing to be gay himself. Note to aspiring pop stars: avoid songs like this — oh, and also having your music play automatically on washing machines.

#14: “Like A Boss” (featuring Seth Rogen)
“Incredibad” (2009)
A lovingly gross homage to Slim Thug’s song of the same name, the Lonely Island takes the phrase “like a boss” in an entirely new direction. A corporate drone, played by Seth Rogen, sits down for an annual review with a “boss” at an unspecified corporation, and almost immediately gets way more than he bargained for. Andy Samberg’s “boss” begins by describing what sounds like a fairly routine office job and quickly goes off the rails — to give you an idea, his “average day” ends with an aerial assault on Russia before flying into the sun and dying. We hope Samberg’s department isn’t taking applications.

#13: “Shy Ronnie 2: Ronnie & Clyde” (featuring Rihanna)
“Turtleneck & Chain” (2011)
Look, we love the first “Shy Ronnie” as much as the next YouTube listicle giant. But its sequel ratchets the ridiculousness up to a whole new level. For some reason that even she admits that she can’t understand, Rihanna’s “Clyde” recruits Andy Samberg’s Shy Ronnie to pull off an old-school bank heist. Of course, things don’t go even remotely as planned thanks to Shy Ronnie’s… well, shyness. While it ultimately works out for “Clyde,” who brings home Jon Hamm as a new beau, we’re left wondering if Ronnie makes it out alive. If his shockingly adept rap skills don’t keep him out of prison, we’re not sure what will.

#12: “3-Way (The Golden Rule)” (featuring Lady Gaga & Justin Timberlake)
“The Wack Album” (2013)
You have to hand it to them: the Lonely Island knows how to not only put together a genuinely great pop song, but also how to act as a magnet for incredible talent. In this case, that would be recurring guest Justin Timberlake, who reprises his role as… What are these guys’ names again? Anyway, that’s secondary — Gaga manages to steal the show from Samberg and Timberlake’s hopeless, clueless loverboys while doing her best ‘80s Madonna impression. You’ll need to watch this one through, oh, we don’t know, maybe a hundred or so times in order to catch all of its perfectly period-accurate references. With a hook that catchy, we don’t think you’ll mind.

#11: “Motherlover” (featuring Justin Timberlake)
“Turtleneck & Chain” (2011)
Don’t worry, this definitely isn’t the last time you’ll be seeing these legendary perverts on our list. For now, though, this song is another notch in the Lonely Island’s comedic belt: that is to say, “Motherlover” is perhaps the raunchiest “SNL” sketch that’s ever made it to air, but it also works by itself as a legitimately catchy song. Released from prison following a stint for — what else? — indecent exposure, Samberg and Timberlake realize that Mother’s Day is afoot and they haven’t done anything to commemorate the holiday. Fortunately for them (and for us), they think of something. We can’t repeat any of that “something,” so we think we’ll just let them do the talking.

#10: “Boombox” (featuring Julian Casablancas of The Strokes)
“Incredibad” (2009)
A boombox can change the world… but it can also make for a cringe-factor far beyond what’s expected in a typical dance song. The Lonely Island often start with a concept not uncommon in whichever genre they’re emulating, and take it to ridiculous extremes that are sure to produce chuckles, belly laughs, and oftentimes discomfort; as exemplified in this songs final verse. We’ve all heard songs about dancing, letting loose, and throwing social norms to the wind, but do we still stand by those sentiments when it involves old people and debauchery? Perhaps not. Either way, “Boombox” is a hallmark example of The Lonely Island’s tendency for taking things to ridiculous extremes.

#9: “Finest Girl (Bin Laden Song)”
“Popstar: Never Stop Never Stopping” (2016)
The talent behind Lonely Island has managed to infiltrate the music industry, television, and of course, The Silver Screen—with Pop Star: Never Stop Never Stopping serving as a shining example of the latter. Andy Samberg’s larger than life pop star persona managed to make fun of many aspects of the entertainment industry, particularly with the song Equal Rights lampooning self-centered social activism, but Finest Girl takes the cake for its uncomfortable and unnecessary sexual euphemisms surrounding the killing of Osama Bin Laden. A handful of friendly faces from the SNL cast made this performance even more enjoyable; as the pop star draws a parallel between getting down and dirty and the execution of one of the 21st century’s most notorious terrorists.

#8: “Threw It on the Ground”
“Incredibad” (2009)
Oh, to be a fly on the wall when this idea was first pitched. Instead of slowly devolving into ridiculousness, this song decided to start there and eventually peppered in a taser to the butthole for good measure. The little things like Samberg’s meticulously crafted goatee underscore the big things… like ruining a child’s birthday party. Of course the icing on the cake comes from the epic cameos of Elijah Wood and Ryan Reynolds. Seeing Jake Perolta get beaten down by Deadpool and Frodo Baggins is quite simply magic.

#7: “We Like Sportz”
“Incredibad” (2009)
With Andy Samberg’s larger than life comedic personality, it’s sometimes easy to forget that The Lonely Island is a trio… and Jorma and Akiva are equally hilarious in front of the camera. Their “2 Guyz” act is a great reminder of this, and also a less than subtle jab at those kids in high school who tried a little too hard to be a part of the jock squad. T-shirts just a little too big, an extreme hatred of cheating, and some unnecessarily crude language towards Steve; We Like Sportz exceeds by lampooning an unexploited niche of social awkwardness.

#6: “I’m On A Boat” (featuring T-Pain)
“Incredibad” (2009)
In terms of pure musical talent, this may very well be their most captivating song. The jokes are few and far between for a Lonely Island song, but the flow is oh so catchy. It’s made appearances in clubs, house parties, and Spring Breaks galore; each time ensuring that the roof is brought down by the song’s end. T-Pain’s remarkable guest performance adds to its enjoyment, and the chorus is easy to shout along with; even for those among us who are several drinks in. We feel a little bad that Jorm wasn’t invited along for the ride; it certainly was a memorable one.

#5: “Lazy Sunday” (featuring Chris Parnell)
“Incredibad” (2009)
In a time when overnight YouTube sensations were not yet a common thing, The Lonely Island changed the game with their second digital short—Lazy Sunday. The unknown group had their big break on Saturday Night Live, and a two-minute song about nothing solidified their popularity for years to come. We’ve all had lazy Sunday afternoons, most of us have snuck food into theaters, and some of us may have even crushed pre-movie trivia. The trio proved that larger than life tales aren’t needed for musical success; just a dope hook and some sweet nothings that we’ve all experienced. The rest is history.

#4: “Jack Sparrow” (featuring Michael Bolton)
“The Wack Album” (2013)
You might think that you’re a cinephile, but you’ve got nothing on Michael Bolton! The Lonely Island set out to make an archetypal song about scoring chicks at the club, but Bolton was too enamored with the Pirates of the Caribbean saga to contribute another cliché party hit. Juxtaposing their efforts with his oblivious dedication to classic adventure movies is a unique concept that allows for hilarious misunderstandings. They never quite reach an agreement on artistic intent and once again, Lonely Island reigns supreme within the areas of the hilariously inexplicable.

#3: “I Just Had Sex” (featuring Akon)
“The Wack Album” (2013)
Have you ever felt the urge to tell the world about getting lucky, just minutes after it’s happened? The Lonely Island and special guest Akon most certainly have, and this ludicrous masterpiece does just that in a ridiculous fashion. Best friends, strangers, even parents? Why not let them all know about your sexual exploits? Nothing, and nobody is off limits in this free spirited expression of success in the bedroom. It’s hard not to share in their joyful celebration, as thousands of New Yorkers do just that, and we’re left wondering why bother keep any aspect of our personal lives secret when they’re having so much fun doing just the opposite.

#2: “Jizz In My Pants”
“Incredibad” (2009)
It should come as no shock that the trio’s nature could be described as sophomoric. Does any song exemplify this fact better than this one? We highly doubt it. Just the many expressions of bewilderment when the unthinkable happens make this song side-splittingly funny. The serious nature and the “no smiles here” mentality make it even better. Is it relatable, or so out there it’s hard to do anything other than laugh? We’d prefer not to speculate, but years later it’s still one of their most hilarious and oddly catchy songs.

#1: “Dick in a Box” (featuring Justin Timberlake)
“Incredibad” (2009)
Andy Samberg is joined by Justin Timberlake to make fun of schmoozy love songs by, well, performers like Justin Timberlake. The duo is unapologetic, and completely oblivious to anything resembling a social norm, and they proceed to give romantic advice that unsurprisingly gets them in to quite a bit of trouble. While their misdirected efforts at a thoughtful Mothers Day present are comparably hilarious, this might be The Lonely Island’s best work yet. When it comes to catchy music, with famous celebrities that leaves you in stitches due to its hilarity, The Lonely Island reigns supreme.

What’s your favorite Lonely Island song? Let us know in the comments below!