Top 10 Best Funny Comedy Songs of All Time

Music can explore deep, weighty subjects, like the agony of heartbreak, or the political issues of our troubled times. But sometimes we just want our music to forget all that and be funny. There have been a lot of musicians through the years who specialize in comedy, from piano playing funnyman Tom Lehrer to Weird Al Yankovic, the King of Parody himself. And then there have been songs from more “serious” artists who decided to let down their hair and go straight for the silly. So get ready for a belly laugh and dive into our picks for the top ten funny comedy songs of all time!

Comedy Song Top 10 Best Funny Comedy Songs of All Time

List of Top 10 Best Funny Comedy Songs of All Time until in 2017

10. Stacy’s Mom – Fountains of Wayne

Let’s start off with Fountains of Wayne and their Grammy-nominated hit “Stacy’s Mom.” Fountains of Wayne’s music is often humorous, but this tale of an underage boy lusting after the mom of the girl next door hit it big, reaching 21 on the Billboard Hot 100. The kid’s over-the-top fantasies remind us of what it’s like to have that first ridiculous crush on some hot supermodel or hunky actor. And as a plus, the video is totally hilarious.

9. Another Irish Drinking Song – Da Vinci’s Notebook

Da Vinci’s Notebook is a comedic a cappella singing group that formed in 1993, and Another Drinking Song is one of its most well-known works. The tune was used in Despicable Me 2, although the lyrics were changed to Minion-speak. The original lyrics gleefully satirize the Irish stereotype of heavy drinking, drunken fighting, and black humor. Lift a glass of Guinness and sing along.

8. Jack Sparrow (feat. Michael Bolton) – The Lonely Island

The Lonely Island is a group comprised of Akiva Schaffer, Andy Samberg, and Jorma Taccone. They started off making short absurdist comedy films and posting them on the internet. In 2005 they were all hired by Saturday Night Live as writers, and Andy Samburg became part of the show’s cast. They are probably best known for their SNL Digital Shorts, which includes the wildly popular “D*ck in a Box.” For our money, though, their best is “Jack Sparrow,” which has the three collaborating with Michael Bolton. The trio want to do a gangsta song about partying at a club, but Bolton, fresh off a Pirates of the Caribbean marathon, just can’t stop singing about Jack Sparrow. We dare you to watch it without giggling.

7. Re: Your Brains – Jonathan Coulton

Jonathan Coulton specializes in songs that celebrate geek culture, from video games (“Still Alive” was written for the end credits of Portal) to computer programming (“Code Monkey” bemoans the hard life of a simple simian programmer). The best is “Re: Your Brains,” which asks what mundane office life would be like if your co-workers turned into zombies. (We chose this video of the song being performed in ASL because the guy acting out the lyrics makes it that much funnier.)

6. The Masochism Tango – Tom Lehrer

In addition to being a musician, Tom Lehrer is a Harvard educated mathematician, political scientist, and satirist. His songs, always sung while accompanying himself on the piano, are whip smart and feel like he’s sharing an inside joke with his audience. You might have heard of “The Elements” (the periodic table set to Gilbert & Sullivan’s “Modern Major General”) or “Poisoning Pigeons in the Park,” but this song tops them all. It’s wickedly funny, reveling in the joys of when love hurts so good.

5. They’re Coming to Take Me Away, HAHA! – Napoleon XIV

Napoleon XIV is the stage name of Jerry Samuels, a singer and songwriter who is mostly known for songs he wrote for other people, including Sammy Davis Jr.’s top 20 hit “The Shelter of Your Arms.” This song was his one hit wonder, peaking at #3 on the Billboard Hot 100, and was a staple on the Dr. Demento radio show. It’s a giddy frolic into insanity that will have you chanting along with the chorus. This is one amongst the Top 10 Best Funny Comedy Songs of All Time until 2017.

4. A Boy Named Sue – Johnny Cash

Johnny Cash, affectionately known as “The Man in Black,” is well known for his gritty country western music. He famously recorded a live album at Folsom prison, which featured “Folsom Prison Blues,” a song that contains the most hardcore lyric in all of country music: “I shot a man in Reno just to watch him die.” You might think he’d be the last person to appear on this list. But in another live album recorded in a prison, San Quentin this time, he introduced “A Boy Named Sue,” a song about a man seeking vengeance on his absent father purely because he had the nerve to name his son Sue. It’s hilarious, and made all the better watching Cash grinning as he sings it, and the inmates laughing as they listen.

3. The Scotsman – Mike Cross

This song has been covered (sometimes as “The Drunken Scotsman”) by a number of artists, including the Irish Rovers. However, it was Mike Cross, an American singer-songwriter, who first penned this tale about a pair of young women who stumble on a Scotsman drunk and passed out on the side of the road and decide to see if the rumors that Scotsmen wear nothing beneath their kilt are true.

2. The Lumberjack Song – Monty Python

Monty Python is the seminal comedy troupe, forever changing the comedy landscape through their TV show Monty Python’s Flying Circus and movies such as Monty Python and the Holy Grail and Life of Brian. Music has played a key role in their comedy, popping up in their sketches, their movies, and their albums. “The Lumberjack Song” is probably the most well-known. First appearing in the ninth episode of Monty Python’s Flying Circus in 1969, this song about a man’s earnest desire to be a lumberjack, cutting down trees and wearing women’s clothing, has been performed many times in many forms, including at the Concert for George, a tribute concert held on the one year anniversary of the death of Beatle George Harrison, a Monty Python devotee.

1. White & Nerdy – Weird Al Yankovic

It probably comes at no surprise that Weird Al, the undisputed king of musical comedy, tops our list. It’s nearly impossible to pick one song out of the literally hundreds he has recorded (if you’d like to marvel at Weird Al’s incredible output over his 40 year career.

We could fill this whole list with Weird All songs and still have some left over we’d wish we could include! How can we forget “Eat It”, or “Like A Surgeon”? For this list, though, we’ve chosen a more recent song: “White & Nerdy” from his 2006 album Straight Outta Lynwood. This song, a parody of “Ridin'” by Chamillionaire and Krayzie Bone, is a gleeful celebration of all that is nerdy. Whether you laugh with it or laugh at it, it’s our pick for the best funny comedy song of all time until 2017.

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