Top 10 Best Lonely Island Songs

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.  

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 Ladin. 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.  

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)

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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" feat. T-Pain Incredibad (2009)

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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.  

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” feat. Michael Bolton Turtleneck & Chain (2011)

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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” feat. Akon Turtleneck & Chain (2011)

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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.  

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.   Before we unveil our number one pick, here are a few honorable mentions.   “Spring Break Anthem” The Wack Album (2013)   “Great Day” Turtleneck & Chain (2011)   “Like a Boss” 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.  Do you agree with our list? What Lonely Island song is your favorite? For more uproarious Top 10s, be sure to subscribe to WatchMojo.com