My Fave Five: The Lonely Island Songs

Story posted November 30, 2022 in CommRadio, Arts & Entertainment by Sophia D’Ovidio

Comedy/fake-rap/production team The Lonely Island is one of comedy's most subtly impactful groups. Made up of Andy Samberg. Akiva Schaffer and Jorma Taccone, who became friends in junior high, rose to stardom after their “SNL: Digital Shorts.”

Many of these digital shorts featured the group parodying musicians, particularly rap. The three always stated that their goal was to make their songs funny but not bad.

Between proper respect and adoration for musicians and access to great artists from their time on “SNL,” The Lonely Island has put out some of the most entertaining, funny, nonsensical bangers out there.

“Finest Girl” - The Lonely Island

Written for the trio’s movie “Popstar: Never Stop Never Stopping,” Samberg plays popstar Connor4Real. In this satire of a pop star, Samberg sings about his relations with a girl, comparing it rather insensitively to the assassination of Osama Bin Laden.

This song is absolutely absurd and extremely weird; it’s also awesome. The Lonely Island knows how to subvert expectations, and the music is catchy.

I’ll always enjoy playing this song for someone who hasn’t heard it before.

“I’m On a Boat” - The Lonely Island (feat. T-Pain)

This song received a grammy nomination for Best Rap/Sung collaboration, which is ridiculous but also deserved. The concept is as simple as the name, with Samberg and Schaffer simply singing along with T-Pain about their day on the boat.

Lyrics like “I’m on a boat and, it’s going fast and, I got a nautical themed Pashmina Afghan” are hysterically clever.

The song is addicting, witty and the perfect song for a boat day, duh.

“Jack Sparrow” - The Lonely Island (feat. Michael Bolton)

The Lonely Island typically makes themselves the butt of the joke, but in “Jack Sparrow,” Michael Bolton gets the laughs.

Bolton insists on writing his verses about “Pirates of the Caribbean” rather than offering a hook for The Lonely Islands' “club banger.”

It’s not just a great joke, but The Lonely Island’s verses are genuinely good, which they need to be for the joke. Mix in Bolton’s vocals and the track itself; it just doesn’t get better.

“Mona Lisa” - The Lonely Island

Another addition from The Lonely Island's “Popstar: Never Stop Never Stopping” soundtrack and the only one on this list without an “SNL: Digital Short” is the catchiest of them all.

“Mona Lisa” is such a stupid joke that it makes it even funnier. The song’s premise is simply that Connor4Real thinks that the Mona Lisa is stupid and ugly.

As expected, it’s a banger and a great reminder that “Popstar: Never Stop Never Stopping” is one of the greatest comedies ever made.

“Motherlover” - The Lonely Island (feat. Justin Timberlake)

Maybe, The Lonely Islands' most iconic collaboration is their work with Justin Timberlake.

Timberlake is one of the best “SNL” hosts to do it, and it has a big part to do with the musical trilogy he created with The Lonely Island.

“Motherlover” is the second installment of that trilogy where Timberlake and Samberg characters decide they will “do” each other's mothers, so each of their moms has a mothers day gift.

The storytelling in this song's lyrics is more impressive than many legitimate musicians.

The R&B/pop track makes “Motherlover” one of the most iconic Lonely Island and “SNL” bits of all time.


Sophia D’Ovidio is a second-year majoring in digital and print journalism. To contact her, email