The Lonely Island’s 10 Most Underrated Music Videos

The Lonely Island might just be the most successful fake musical group in history. Sure, Andy Samberg, Jorma Taccone and Akiva Schaffer got their start spitting rhymes about their Sunday plans and crooning about inside-the-box gift ideas with Justin Timberlake, but the former YouTube-stars-turned-SNL-stars are no joke.

Their three studio albums have sold a combined 744,000 copies. “I Just Had Sex,” featuring Akon, charted as high as 30 on the Billboard Top 100. Their rap video parody “I’m on a Boat” went double-platinum, earning the group a Grammy nomination. (Really.) And they’ve collaborated with everyone from Kendrick Lamar to Michael Bolton along the way.

Now, the Lonely Island crew is putting their signature ability to make legitimately catchy hits out of the dumbest possible song ideas to good use with Popstar: Never Stop Never Stopping, a mockumentary starring Samberg as Connor4Real, a pop megastar with millions of fans, a 32-person entourage and zero musical talent (so, Bieber, basically).

So, with both the movie and its soundtrack dropping Friday, we’re looking back at some of the group’s greatest music videos… that you haven’t already watched a thousand times on YouTube. Because c’mon, anyone can make a list featuring “Jack Sparrow” and “Like a Boss.” Here are a few of TLI’s lesser-known hits and deep cuts to get you hyped for Popstar.

Iran So Far

The group’s official follow-up to the Emmy-winning “Dick in a Box” (again: really) didn’t end up charting quite as well. Probably because it was a piano-heavy love song to Iranian president Mahmoud Ahmadinejad, and that punny title pretty much screams, “We wrote this at 3 AM Friday morning.” But getting Adam Levine to cameo totally sells the cheesy ballad vibes; plus, we’re awarding bonus points for the chorus of children and the sight of Fred Armisen as Ahmadinejad in a red lounge singer dress.

Best Line: “You can deny the Holocaust all you want/But you can’t deny that there’s something between us.”

Cool Guys Don’t Look at Explosions

Originally made for the 2009 MTV Movie Awards — which Samberg hosted — this is vintage Lonely Island: poking fun at a pop culture clichés while simultaneously parodying overblown soft rock ballads. Featuring Samberg as a Springsteen lookalike, Will Ferrell as Neil Diamond and J.J. Abrams on the keyboard (because, sure, why not), it also pretty much ruined all our favourite action hero moments by pointing out just how ridiculous they are. Thanks a lot, guys.

Best Line: “The flames are hot, but their heart is chill.”

We Like Sportz

Samberg’s been the frontman for most of the group’s biggest hits, but the “Just 2 Guyz” saga is all Jorma and Akiva. Started back when the trio were just up-and-coming YouTube stars, the intentionally terrible rap series is now going on four installments. But we’re especially partial to the sequel, “We Like Sportz,” where the two rap super-convincingly about their love of all things sports and show off their mad dog faces.

Best Line: “If my team loses, I’ll be mean all night/If you tell me to relax, we’ll get in a fight.”

Diaper Money

Making swagger-filled rap videos about the least brag-worthy subjects possible is one of the Lonely Island’s signatures. It’s the central concept behind so many of their iconic singles: “Lazy Sunday,” “I’m on a Boat,” “Like a Boss,” and this one you might have missed, where the three rap about serious “grown-man sh*t.” Diapers and grave plots have never sounded more badass.

Best Line: “You afraid of death?/Well, I’m afraid not/’Cuz I got the bomb spot, right off the highway.”

Spring Break Anthem

The appropriately-titled “Spring Break Anthem” is an air horn-filled ode to all those classic Spring Break moments – you know, like crushing beers, wet t-shirt contests, and marrying a dude. The video features cameos from Zach Galifianakis, James Franco, Edward Norton, and a bunch of rowdy spring breaker bros who presumably had no idea they were also starring in an anthem dedicated to gay marriage.

Best Line: “SoCo in my canteen, got girls jumpin’ on a trampoline/Two men bound by the law!”

Great Day

After originally debuting as an SNL Digital Short, “Great Day” made it onto the Lonely Island’s sophomore album Turtleneck & Chain (which was Billboard’s #1 rap album the week it debuted, just FYI). Despite that fact, this song is essentially every overblown musical number you’ve ever seen, only starring a coked-out businessman who’s rapidly losing his damn mind. So, in other words, it’s the best musical number ever. (Sorry, Hamilton.)

Best Line: “Something today makes me feel fine and fancy free/Much of the ocean is still unexplored/How did I get up in this tree?”

Boombox

Featuring Julian Casablancas of The Strokes, a magical boombox, and some pretty dope fingerless gloves, this single from the Lonely Island’s debut album took a while to get the Digital Short treatment, but by all rights, it should’ve been instant classic. After all, it’s the ultimate cautionary tale about the power of music, dancing, and comedy’s rule of threes. A boombox is not a toy, people.

Best Line: “The music washed away their hate, and society started dancing/Every demographic was represented, it was a Rainbow Coalition of dancing.”

Reba (Two Worlds Collide)

Thanks to the Lonely Island’s success, they’ve been able to land some huge names to guest on their tracks over the years, from Snoop Dogg to Lady Gaga. …And then there’s the time Samberg dueted with country music legend Reba McEntire – or rather, a dude in a wig sort of, kind of, but only barely pretending to be Reba McEntire. Just a heads-up: this one is downright filthy. It’s also downright hilarious.

Best Line: “My friends think I should dump her/They say she’s a man who found a wig in a dumpster.”

Hugs

You can have “Motherlover” — this is hands-down the best Lonely Island song about loving up on other peoples’ moms. As far as we can figure, the only reason “Hugs” doesn’t rate higher in the Lonely Island pantheon is because most people had already stopped watching SNL by the time it aired, when Samberg returned to host the Season 39 finale. Otherwise, this song is so genuinely catchy, it could’ve easily been considered one of the best singles of 2014. You know, if it wasn’t entirely about hugs, that is.

Best Line: “I’ll hug a girl like it don’t mean nothing/Then turn around and start hugging her cousin.”

Ras Trent

When I go to close my eyes at night, this is the one Lonely Island song that continues to haunt my dreams: a classic reggae parody about white dudes with dreads and only a passing understanding of Rasta culture. Everything about it is pitch perfect, from Samberg’s terrible singing, to his baja hoodie and the legitimately clever Angela Lansbury joke. Like so many of Lonely Island’s cleverly-crafted parodies, it is quite possibly the best fake reggae song of all-time. High praise, we know.

Best Line: “Me toil part time at jah Cold Stone Creamery.”