5 Funniest Songs by The Lonely Island

The combination of laughter and music may not always lead to success, but as a handful of iconic musical comedy acts have proven, the result certainly can have mainstream appeal. For instance, the last decade has seen The Lonely Island grow from a Saturday Night Live highlight to a Grammy-nominated multi-platinum trio — comprised of Andy Samberg, Akiva Schaffer, and Jorma Taccone — with several ubiquitous hits under its belt. This year, The Lonely Island will headline Popstar: Never Stop Never Stopping, a big-screen comedy produced by Judd Apatow. [Update, 3/1/16: Changed title from ‘Conner4Real’ to ‘Popstar: Never Stop Never Stopping’.] As its release draws near, we look back at the funniest tunes ever released by The Lonely Island.

5. “Dick in a Box”

The Lonely Island initially made its debut with a series of “digital shorts” on Saturday Night Live, and this holiday-themed serenade served as their breakout hit. Featuring Justin Timberlake, the track features the former N’Sync frontman and Samberg sharing vocals in the style of an early 1990s R&B ballad. The video for the song went viral, becoming a top 10 hit on the comedy charts and winning an Emmy in the process, easily eclipsing The Lonely Island’s first hit, 2005 release “Lazy Sunday.”

4. “I’m on a Boat”

If “Dick in a Box” was the general public’s introduction to The Lonely Island, this sea-faring hip hop parody — featuring auto-tuned rhymes courtesy of then-omnipresent T-Pain — represents the group at the heights of its powers. The song topped the comedy charts, and its accompanying short film brilliantly lampoons many clichés running rampant in rap videos. For the most part, The Lonely Island’s career is built around poking fun at hip hop, and to that end, “I’m On a Boat” might just be the trio’s crowning achievement.

3. “Motherlover”

The Lonely Island reunites with Timberlake for this sequel to “Dick in a Box”, which sees the two balladeers deciding to seduce each other’s mothers. Listeners who find that premise itself offensive should probably avoid “Motherlover,” but for the rest of us, the song is so unabashedly shameless in its indecency that it’s impossible to take seriously. Moreover, the video features actresses Susan Sarandon and Patricia Clarkson (who starred with Timberlake in Friends with Benefits) as the mothers in question. Enjoy at your own risk; you may end up with some terribly inappropriate lyrics stuck in your head.

2. “Threw It on the Ground”

One of the more underrated efforts by The Lonely Island, this song is a solo for Samberg, who plays a man so self-assured in his manhood (“[he’s] an adult!”) that he often demonstrate his empowerment by throwing various items on the ground, hence the title. Samberg’s committed performance both on the song and in its video is so over-the-top that chuckles are inevitable. Keep your eyes peeled for memorable cameos by Elijah Wood and Ryan Reynolds as the “Hollywood phonies” that revolt against Samberg’s childish protagonist.

1. “Jack Sparrow”

In the late 1980s, Michael Bolton’s signature pop power ballads shot to the top of music charts. However, no one expected the singer-songwriter to share the mic with The Lonely Island. In doing so, Bolton demonstrates a keen sense of humor, poking fun at his own vocal style while name-checking various elements of the Pirates of the Caribbean franchise (“Keira Knightley!”). The result is an off-the-wall collaboration that might be the best guest appearance in any Lonely Island track thus far, topping tracks with Lady Gaga, Lil Jon, and Nicki Minaj.

Per the official The Lonely Island Twitter account, Popstar: Never Stop Never Stopping will land in theaters on June 3.


Follow Robert Yaniz Jr. on Twitter @CrookedTable.

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