3 Sad Songs Written by Normally Funny People We Sing Along To

Art is often about juxtaposition. Often, the best artists know how to flip things on their head. They’re subversive, they’re creative. They take what they see in the world and upend it. And here below, that’s just what we wanted to explore. We wanted to dive into three songs from artists that truly make us feel something. But it’s a sensation we wouldn’t expect given who is delivering it. Indeed, these are three sad songs written by normally funny people we sing along to.

Videos by American Songwriter

“A Better Son/Daughter” by Rilo Kiley from ‘The Execution Of All Things’ (2002)

Indie rock fans from the early 2000s remember—Rilo Kiley was it. The group, which was fronted by Jenny Lewis and Blake Sennett, offered fans a particularly keen insight into what it meant to be alive at the turn of the millennium. The band was clever and often funny. But on “A Better Son/Daughter”, Rilo Kiley was especially poignant. The sad offering was triumphant. As it talked about a parent with mental illness, listeners enjoyed a bit of tearful humor from Lewis. It’s a wondrous work and worth revisiting often.

“Are You Happy?” by Bo Burnham from ‘Make Happy’ (2016)

Comedian Bo Burnham has won the hearts of many fans thanks to his insightful, nuanced brand of comedy. Burnham obviously has a depth of feeling, and he’s more than capable of showcasing it on his various Netflix specials. On “Are You Happy?”, which concludes his 2016 show, Make Happy, Burnham offers a window into his own psyche. Performers know—once the curtain comes down, doubt rises. Did I do a good job? Is the audience satisfied? Are they happy? It’s a hard worry to reckon with, but Burnham does it here with sadness and a little joy.

“Chris Farley Song” by Adam Sandler (Single, 2019)

For as funny as he can be, Adam Sandler is also often reflective and melancholy. It’s this unique character trait that made him well-suited for the tragicomic 2009 movie, Funny People. He also displays it admirably a decade later in the 2019 ode to his late friend, comedian Chris Farley. On “Chris Farley Song”. Sandler reminisces. He recalls with a tear in his eye the moments of meeting Farley, watching him, and performing with him. It’s a beautiful homage.

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