4 Pop Songs That Are So Bittersweet, Listening to Them Hurts and Feels Good All at Once

Pop music is, in its purest form, entertainment, and more often than not, we use entertainment to feel happy, excited, and empowered. Sad songs are full-blown tear-jerkers. Angry songs are aggressive, “I’ll bust the windows out of your car” energy. 

Delicate, nuanced emotions like bittersweetness don’t always find their way into pop music because they’re hard to distill into quippy, catchy hooks. Of course, “hard” doesn’t mean “impossible,” as proven by these four bittersweet pop songs that hurt so good.

“Vienna” by Billy Joel 

Billy Joel’s 1977 track, “Vienna”, from The Stranger is practically the blueprint for bittersweet pop songs. (Especially if you were in the target demographic for 13 Going On 30, if you know, you know.) This easy-listening pop tune reads like a pep talk from someone wiser and older. Not in a condescending way. More in the bittersweet “we both know that I’m right” kind of way.

“American Pie” by Don McLean

Though definitely more folk-rock in flavor, we’d argue that Don McLean’s “American Pie” earned its distinction as a pop song when it spent weeks at the top of the Billboard Hot 100. This ultra-nostalgic song from 1971 paints descriptive pictures of good ol’ days gone by with such clarity that you can also see the marching band refusing to yield to the football team right in front of you.

“If It Makes You Happy” by Sheryl Crow

Sheryl Crow wrapped up the paradox of bittersweetness in one catchy chorus with her 1996 pop hit “If It Makes You Happy”. “If it makes you happy, it can’t be that bad / If it makes you happy, then why the hell are you so sad?” Such is the way with bittersweet emotions. You’re happy and sad all at once in a chaotic whirlwind of opposing feelings.

“Fast Car” by Tracy Chapman

Before Luke Combs put out his award-winning rendition of “Fast Car”, Tracy Chapman blessed the world with the original in 1988. The folky pop tune perfectly encapsulates the wistfulness of daydreaming of a better life while still acknowledging the reality of one’s current existence. It’s hopeful and melancholic all at once. In a word, bittersweet.

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