Top 10 Broadway Songs That Are Tragically Funny

The nominees for Worst Life are: a recent college graduate with an English degree, a kindergarten teacher who can’t get a date, an unemployed comedian, two roommates with completely contrasting habits, a therapist who can’t find work, a literal monster with a proclivity for adult films, and former child star Gary Coleman. “It Sucks to Be Me” sees the puppet denizens of this edgy-for-its-time 2003 musical engage in a debate about whose life sucks the most. Although the world of the show is stylized, the lyrics just hit in some of the most uncomfortable ways. On top of many important life lessons, “Avenue Q” taught us that one thing everyone has in common is that they think they have it the worst.

This meta-musical is a parody of a genre of classic shows from the early 20th century. In it, the title character is given a rollicking anthem to alcohol as an answer to life’s troubles, disappointments, and confusions. Why worry about anything when there’s whiskey and wine to be drunk? We get the sense that the chaperone’s viewpoint is that life is too disappointing to face without a little liquid courage. It’s great for how blatant it is and also because it’s at least a little relatable. What do you do when life is overwhelming, or even underwhelming? Maybe the answer isn’t alcohol, but you’ve got to find something you enjoy, even if it’s just a distraction from the misery.

The eponymous spelling bee of this off-kilter musical comedy serves as a backdrop for the anxieties and pressures its middle schooler characters go through. For example, Marcy is an overachiever who can’t help but succeed, despite feeling no sense of fulfillment when she does. But Chip Tolentino has what is possibly the most awkward – and funniest – problem. He loses the bee all because of a badly-timed surge of hormones. It’s the kind of song that makes you remember all the worst parts of being young, and laugh because at least it’s not you going through it anymore.

Elle Woods is thrown for a few loops between the laughs. Her desire to be more “Serious” and less blonde leads her to Paulette, a beautician with words of wisdom. Inspired by her love of an Irish folk CD called “Celtic Moods,” the entire nation of Ireland comes to stand in for Paulette’s hope of something better. To her, Ireland is the land of love, leprechauns, and dancing without using your arms. As ridiculous as some of it is, her naive hope is really touching, especially when she tells Elle that even if she never gets to see Ireland, Elle will.

Adelaide is a nightclub performer with a persistent cold. Like many a WebMD user after her, she’s made her own self-diagnosis. Her conclusion, that her symptoms are a psychosomatic response to her fiancé refusing to marry her, makes up one of classic musical theater’s best and most beloved songs. The now-classic tune features several clever turns of phrase and wordplay as Adelaide gives us her own personal translation of a jargon-filled medical textbook. Attacks of sneezing, sniffles, and hacking punctuate her hopelessness. Though its references are dated, it’s hard not to feel for Adelaide, because the fact remains she’s definitely with a guy who’s scared to commit and she’s not sure how much longer she can wait.

Annie is an orphan trying to escape from an orphanage. Miss Hannigan is the tyrannical matron of the orphanage who despises children. Luckily, composer Charles Strouse and lyricist Martin Charnin make sure to bring the funny to what sounds like it could be an awfully miserable show on paper. The show’s humor is most represented by this song, which finds Annie and the other children performing a choreographed deep clean of the orphanage. They sing about their lot in life, which is admittedly not great. They muse about not having enough food and not knowing who Santa Claus is. It’s as depressing as it is charming.

Mrs. Lovett commits a lot of crimes in this legendary musical. Yes, there’s the cannibalism, but her cooking might be the most egregious crime of all. Business is not going well for the owner and operator of a woebegone Fleet Street pie shop when we first meet her. She’s clearly at the end of her rope. “The Worst Pies in London” is an anthem to just how terrible she is at her job. Her pies taste like garbage, they look like something that crawled out of the gutter, and they’re overall just really unfit for human consumption. If she’s looking to switch fields, may we suggest advertising?

Amos Hart is not exactly the world’s luckiest man. His wife was running around on him, and he only found that out because she killed the guy she was running around on him with. Oh, and he’s on the hook for her lawyer bills. Despite all the craziness happening around him, Amos is not a very interesting man. There’s just something about him that makes people look right past him. “Mr. Cellophane” is the only song he gets to himself. What’s worse is it makes us realize he knows how he looks to people. He even ends the number with a line demonstrating just how much he’s used to feeling like a burden.

When her husband leaves her for another man, Trina takes it about as well as a person can… If that person is absolutely losing their grip on reality. Trina erupts into a devastatingly funny and dangerous number in the middle of preparing her famous “banana-carrot surprise”. She volleys between rage and despair, panic over her new situation and some very warranted confusion. At one point, she even pleads to the audience for help. “I’m Breaking Down” is a feat of vocal, psychological, and physical dexterity that touches on virtually every human emotion you could possibly think of.

Before we unveil our top pick, here are a few honorable mentions.

“Model Behavior,” “Women on the Verge of a Nervous Breakdown”
Candela Might Be Dating an International Terrorist & Her Best Friend Won’t Return Her Call

“When He Sees Me,” “Waitress”
Dawn Tries Online Dating & Imagines the Worst

“The History of Wrong Guys,” “Kinky Boots”
Lauren Gets a Promotion & a Crush on Her Boss

“Diva’s Lament (What Ever Happened to My Part?),” “Spamalot”
The Lady of the Lake Expresses Her Frustration at the Writers

This song is the counterpoint to this Sondheim show’s ambivalent, but ultimately hopeful perspective on marriage. It’s about a bride-to-be getting cold feet, and the absolute trainwreck of anxiety, doubt, and self-loathing that follows. Amy’s stream of consciousness is put to frantic music at a pace that would tongue-tie the most adept vocalists. Also deserving of a mention is “The Ladies Who Lunch,” which gets a lot of the glory for its darkly humorous and merciless skewering of a certain class of women. It’s “Getting Married Today,” however, that touches on so many sad and terrifying ideas in such a short amount of time that you can’t help but laugh. By the end of it, Amy is ready to happily submit to what she just called a horrifying and prehistoric ritual.