5 of the Most Hilarious Songs of All Time

Need a little pick-me-up? It’s pretty undisputed that the world has gone to crap recently, and finding joy in the little things might be the only thing to keep most of us afloat. And there’s nothing quite like a comedic song to get you through the day. Let’s take a look at five of the most hilarious songs of all time!

1. “Wonderboy” by Tenacious D

Musically, this is a killer song. Foo Fighters’ Dave Grohl is on the drums, Jack Black is being Jack Black, and Kyle Gass debuts his killer guitar-playing skills for the first time on Tenacious D’s debut single “Wonderboy”. But outside of musicality, it’s also a very hilarious track. The music video is essential viewing for any lover of the absurd.

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2. “I’m On A Boat” by The Lonely Island

Comedy-music trio The Lonely Island were no strangers to penning parody songs back in the day. “I’m On A Boat” was one of their biggest SNL streaming hits in the early aughts, and it’s still pretty hilarious today. We also love that T-Pain agreed to be part of it.

3. “Welcome To The Internet” by Bo Burnham

Bo Burnham’s pandemic special was a rough, emotional watch when it first came out, but it did have its very comedic moments. “Welcome To The Internet” is a very well-written carnival-level acid trip of a song, and it’s also quite hilarious. If you’ve ever spent more than five minutes on social media, you’ll get it.

4. “Carol Brown (Choir Of Ex Girlfriends)” by Flight Of The Conchords

Jemaine Clement and Bret McKenzie don’t shy away from dry humor in Flight Of The Conchords, and they manage to do it with an interesting instrumental backing composed of omnichords, trumpets, and other unusual instruments. “Carol Brown” is one of their funniest songs, and it is the perfect mix of self-deprecating and absurd.

5. “29/31” by Garfunkel & Oats

Comedy duo Garfunkel & Oats managed to nail that weird feeling that happens when you cross the threshold into your 30s. The duet is hilarious and entertaining, loaded with the right mix of hopeful optimism and existential frustration. The ukulele makes it even funnier, somehow.

Photo via Audible Cover Art / Courtesy of Shore Fire Media

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