These Broadway songs prove that a number can be tragic AND funny. For this list, we’ll be looking at hilarious show tunes that have an awkward, sad, or sinister undercurrent.
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00:00 He's a queen, I'm a queen, where is my crown?
00:03 I'm breaking down.
00:04 - Welcome to Ms. Mojo.
00:06 And today, we're counting down our picks
00:07 for the top 10 Broadway songs that are tragically funny.
00:11 ♪ Now denying times is hard, sir ♪
00:16 - For this list, we'll be looking at hilarious show tunes
00:18 that have an awkward, sad, or sinister undercurrent.
00:21 Which of these tragically funny tunes
00:23 had you singing along?
00:24 Let us know in the comments.
00:27 Number 10, "It Sucks to be Me," Avenue Q.
00:31 ♪ It sucks to be broke and unemployed ♪
00:33 ♪ And turning 33 ♪
00:35 ♪ It sucks to be me ♪
00:36 - Do you think your life sucks?
00:38 - I think so.
00:39 - Your problems aren't so bad.
00:40 - The nominees for "Worst Life" are
00:43 a recent college graduate with an English degree,
00:45 a kindergarten teacher who can't get a date,
00:48 an unemployed comedian,
00:49 two roommates with completely contrasting habits,
00:52 a therapist who can't find work,
00:54 a literal monster with a proclivity for adult films,
00:57 and former child star Gary Coleman.
00:59 "It Sucks to be Me" sees the puppet denizens
01:01 of this edgy-for-its-time 2003 musical
01:04 engage in a debate about whose life sucks the most.
01:07 ♪ Oh, every day is an aggravation ♪
01:10 ♪ Hold on, that's an exaggeration ♪
01:13 ♪ You leave your clothes out ♪
01:14 ♪ What are you? ♪
01:15 ♪ You put your feet on my chair ♪
01:16 - Although the world of the show is stylized,
01:19 the lyrics just hit in some of the most uncomfortable ways.
01:22 On top of its many important life lessons,
01:25 "Avenue Q" taught us that one thing everyone has in common
01:28 is that they think they have it the worst.
01:30 ♪ It sucks to be you ♪
01:33 ♪ On Avenue Q ♪
01:35 ♪ On Avenue Q ♪
01:37 ♪ On Avenue Q ♪
01:39 ♪ But it's not when we're together ♪
01:43 - Number nine, "As We Stumble Along,"
01:46 the drowsy chaperone.
01:47 ♪ We look here ♪
01:49 ♪ And we look there ♪
01:51 ♪ Seeking answers anywhere ♪
01:55 ♪ Never sure of where to turn or what to do ♪
02:00 - She was an alcoholic.
02:02 - This meta-musical is a parody of a genre
02:04 of classic shows from the early 20th century.
02:07 In it, the title character is given a rollicking anthem
02:10 to alcohol as an answer to life's troubles,
02:12 disappointments, and confusions.
02:14 Why worry about anything
02:16 when there's whiskey and wine to be drunk?
02:18 - It's a dismal little world in which we live.
02:21 ♪ I can bore you till you've nothing left to give ♪
02:26 ♪ Seven overrated wonders ♪
02:28 ♪ Seven underwhelming seas ♪
02:30 - We get the sense that the chaperone's viewpoint
02:32 is that life is too disappointing to face
02:35 without a little liquid courage.
02:36 It's great for how blatant it is,
02:38 and also because it's at least a little relatable.
02:41 ♪ Blinding sunbeams ♪
02:44 ♪ Rarely knowing right from right ♪
02:48 ♪ Or left from wrong ♪
02:52 ♪ But as long as we can hear ♪
02:56 ♪ That little bluebird ♪
02:58 - What do you do when life is overwhelming
03:00 or even underwhelming?
03:02 Maybe the answer isn't alcohol,
03:04 but you've gotta find something you enjoy,
03:06 even if it's just a distraction from the misery.
03:09 ♪ As we stumble ♪
03:13 ♪ Up ♪
03:15 ♪ Along ♪
03:17 - Number eight, "My Unfortunate Erection, Chip's Lament,"
03:32 the 25th annual Putnam County Spelling Bee.
03:35 ♪ It is tradition ♪
03:39 ♪ That the person eliminated from the competition ♪
03:42 ♪ Is fair game for derision ♪
03:44 - The eponymous spelling bee
03:45 of this off-kilter musical comedy
03:47 serves as a backdrop for the anxieties and pressures
03:50 its middle schooler characters go through.
03:52 For example, Marcy is an overachiever
03:54 who can't help but succeed,
03:56 despite feeling no sense of fulfillment when she does.
03:58 ♪ Winning is a job ♪
04:00 ♪ And she gets no real enjoyment ♪
04:03 ♪ But just a hard lazy flaw ♪
04:07 - But Chip Tolentino has what is possibly
04:11 the most awkward and funniest problem.
04:14 ♪ Adulthood brings its own peculiar rejection ♪
04:19 ♪ Which is why I'm selling this PTA ♪
04:24 ♪ Confection ♪
04:28 - He loses the bee all because
04:30 of a badly timed surge of hormones.
04:33 It's the kind of song that makes you remember
04:35 all the worst parts of being young,
04:37 and laugh because at least it's not you
04:39 going through it anymore.
04:40 ♪ Rejection ♪
04:43 ♪ Me wretched, my unfortunate erection ♪
04:48 - Number seven, Ireland, Legally Blonde.
04:53 ♪ When I'm lonely, I'm feeling dejected ♪
04:56 ♪ I play this and it never fails ♪
05:00 ♪ I pretend like I'm in Ireland ♪
05:05 ♪ With Enya and the whales ♪
05:08 - Al Woods is thrown for a few loops between the laughs.
05:11 Her desire to be more serious and less blonde
05:14 leads her to Paulette, a beautician with words of wisdom.
05:17 ♪ You want the moon and sky ♪
05:19 ♪ Then take it, don't be shy ♪
05:21 ♪ Baby, that's why you and I ♪
05:26 ♪ Should break up ♪
05:27 ♪ Yes, baby, I'll give you my hand ♪
05:29 ♪ Baby, what ♪
05:32 - Inspired by her love of an Irish folk CD
05:34 called Celtic Moods, the entire nation of Ireland
05:38 comes to stand in for Paulette's hope of something better.
05:40 To her, Ireland is the land of love, leprechauns,
05:44 and dancing without moving your arms.
05:46 ♪ Smell the grass as a rainstorm is ending ♪
05:50 ♪ People smile as they stroll past their farm ♪
05:54 ♪ With a red-headed sailor named Brendan ♪
05:57 ♪ And we dance without moving our arms ♪
06:02 - As ridiculous as some of it is,
06:05 her naive hope is really touching,
06:07 especially when she tells Elle
06:08 that even if she never gets to see Ireland, Elle will.
06:12 ♪ Give my love to the leprechauns ♪
06:16 - Number six, Adelaide's Lament, Guys and Dolls.
06:26 ♪ In other ways, just from waiting around ♪
06:29 ♪ For that plain little band of gold ♪
06:32 ♪ A person could develop a cold ♪
06:36 - Adelaide is a nightclub performer with a persistent cold.
06:39 Like many a web MD user after her,
06:42 she's made her own self-diagnosis.
06:44 Her conclusion?
06:45 That her symptoms are a psychosomatic response
06:48 to her fiance refusing to marry her.
06:50 And that makes up one of classic musical theater's
06:52 best and most beloved songs.
06:55 ♪ You can feed her all day with the vitamin A ♪
06:57 ♪ And the bromophys ♪
07:00 ♪ But the medicine never gets anywhere ♪
07:02 ♪ Near where the trouble is ♪
07:05 ♪ If she's getting a kind of a name for herself ♪
07:07 ♪ And the name ain't his ♪
07:09 - The now classic tune features several clever turns
07:12 of phrase and wordplay,
07:13 as Adelaide gives us her own personal translation
07:16 of a jargon-filled medical textbook.
07:18 Attacks of sneezing, sniffles,
07:20 and hacking punctuate her hopelessness.
07:22 ♪ Then they get off at Saratoga ♪
07:25 ♪ For the 14th time ♪
07:28 ♪ A person can develop a grip ♪
07:31 ♪ A grip, a post-sneeze ♪
07:34 - Though its references are dated,
07:36 it's hard not to feel for Adelaide,
07:38 because the fact remains she's definitely with a guy
07:41 who's scared to commit,
07:42 and she's not sure how much longer she can wait.
07:45 ♪ A person can develop a grip ♪
07:49 ♪ A grip, a post-sneeze ♪
07:52 - Number five, "It's the Hard Knock Life," Annie.
07:59 ♪ It's the hard knock life for us ♪
08:01 ♪ It's the hard knock life for us ♪
08:04 ♪ Instead of treated ♪
08:05 ♪ We get treated ♪
08:07 ♪ Instead of kisses ♪
08:08 ♪ We get kissed ♪
08:10 - Annie is an orphan trying to escape from an orphanage.
08:13 Miss Hannigan is the tyrannical matron of the orphanage
08:15 who despises children.
08:17 Luckily, composer Charles Strauss
08:19 and lyricist Martin Charnan make sure to bring the funny
08:22 to what sounds like it could be
08:23 an awfully miserable show on paper.
08:26 ♪ Santa Claus we never see ♪
08:29 ♪ Santa Claus, what's that? ♪
08:30 ♪ Who's he? ♪
08:32 ♪ No one cares for you, a bitch ♪
08:35 ♪ When you're in an orphanage ♪
08:38 ♪ It's the hard knock life ♪
08:40 - The show's humor is most represented by this song,
08:43 which finds Annie and the other children
08:45 performing a choreographed deep clean of the orphanage.
08:48 They sing about their lot in life,
08:50 which is admittedly not great.
08:51 They muse about not having enough food
08:53 and not knowing who Santa Claus is.
08:55 It's as depressing as it is charming.
08:58 ♪ It's the hard knock life ♪
09:02 (feet clomping)
09:03 - Number four, "The Worst Pies in London."
09:06 Sweeney Todd, the demon barber of Fleet Street.
09:08 - A customer!
09:09 ♪ What, what's your rush, what's your hurry? ♪
09:13 ♪ You gave me such a fright ♪
09:14 ♪ I thought you was the ghost of a minicart ♪
09:16 ♪ Sit, sit you down, sit ♪
09:18 ♪ All I meant is that I haven't seen a customer for weeks ♪
09:21 ♪ Did you come in for a pie, sir? ♪
09:23 - Mrs. Lovett commits a lot of crimes
09:25 in this legendary musical.
09:26 Yes, there's the cannibalism,
09:28 but her cooking might be the most egregious crime of all.
09:32 ♪ I know, I know, nobody cares to take them ♪
09:35 ♪ I should know, I make them ♪
09:38 ♪ But good, now, the worst pies in London ♪
09:43 - Business is not going well for the owner
09:45 and operator of a well-begone Fleet Street pie shop
09:48 when we first meet her.
09:49 She's clearly at the end of her rope.
09:51 "The Worst Pies in London" is an anthem
09:53 to just how terrible she is at her job.
09:55 ♪ What I call enterprise ♪
09:57 ♪ Popping pussies into pies ♪
09:59 ♪ Wouldn't do in my shop ♪
10:01 ♪ Just the thought of it's enough to make you sick ♪
10:04 ♪ And I'm telling you, them pussycats is quick ♪
10:07 - Her pies taste like garbage,
10:09 they look like something that crawled out of the gutter,
10:12 and they're overall just really unfit for human consumption.
10:15 If she's looking to switch fields,
10:17 may we suggest advertising?
10:19 ♪ Times is hard ♪
10:22 ♪ Times is hard ♪
10:27 - Number three, Mr. Cellophane, Chicago.
10:32 - If someone stood up in a crowd
10:34 and raised his voice up way out loud
10:37 and waved his arm and shook his leg,
10:40 you'd notice some.
10:42 - Amos Hart is not exactly the world's luckiest man.
10:45 His wife was running around on him,
10:47 and he only found that out
10:48 because she killed the guy she was running around on him with.
10:51 Oh, and he's on the hook for her lawyer bills.
10:53 Despite all the craziness happening around him,
10:56 Amos is not a very interesting man.
10:58 ♪ Cellophane, Mr. Cellophane ♪
11:03 ♪ Shoulda been my name ♪
11:06 ♪ Mr. Cellophane ♪
11:08 ♪ You can look right through me ♪
11:11 ♪ Walk right by me ♪
11:14 - There's just something about him
11:15 that makes people look right past him.
11:17 Mr. Cellophane is the only song he gets to himself.
11:20 ♪ Never even know ♪
11:25 ♪ I'm there ♪
11:33 - What's worse is that it makes us realize
11:37 he knows how he looks to people.
11:39 He even ends the number with a line demonstrating
11:41 just how much he's used to feeling like a burden.
11:44 - Hope I didn't take up too much of your time.
11:46 - Number two, I'm Breaking Down,
11:50 falsettos.
11:50 ♪ Great men will be men ♪
11:54 ♪ Let me turn on the gas ♪
11:58 ♪ I caught them in the den ♪
12:01 ♪ With Marvin grabbing Whizzer's ass ♪
12:05 - When her husband leaves her for another man,
12:07 Trina takes it about as well as a person can,
12:10 if that person is absolutely losing their grip on reality.
12:13 Trina erupts into a devastatingly funny and dangerous number
12:17 in the middle of preparing her famous
12:18 banana carrot surprise.
12:20 She volleys between rage and despair,
12:22 panic over her new situation,
12:24 and some very warranted confusion.
12:27 - Oh yes, it's true.
12:29 I can cry on cue, but so can you.
12:31 I'm breaking down.
12:33 I'm breaking down, down, down.
12:38 You ask me is it fun to cry over nothing?
12:42 It is.
12:42 - At one point, she even pleads to the audience for help.
12:46 I'm breaking down is a feat of vocal, psychological,
12:49 and physical dexterity that touches on virtually
12:51 every human emotion you could possibly think of.
12:54 ♪ The only thing that's breaking up ♪
12:56 ♪ Is my family but me ♪
12:58 ♪ I'm breaking down ♪
13:01 - Before we unveil our top pick,
13:09 here are a few honorable mentions.
13:12 Model behavior, women on the verge of a nervous breakdown.
13:15 Candela might be dating an international terrorist
13:18 and her best friend won't return her call.
13:20 - I know you think I'm overly romantic,
13:22 but you wouldn't believe the connection we have.
13:23 Like immediately, I was ready for him to meet my mom.
13:26 Like I could feel my heart exploding like some kind of bomb.
13:29 Which is ironic because actually I think
13:31 he literally has some kind of,
13:32 anyway, grandpa, happy birthday.
13:34 - When he sees me, waitress.
13:36 Dawn tries online dating and imagines the worst.
13:39 ♪ He can ask me questions about myself ♪
13:41 ♪ He might sit too close ♪
13:43 ♪ Or call the waiter by his first name or eat Oreos ♪
13:47 ♪ But eat the cookie before the cream ♪
13:49 ♪ But what scares me the most ♪
13:51 ♪ What scares me the most ♪
13:54 - The history of wrong guys, kinky boots.
13:57 Lauren gets a promotion and a crush on her boss.
14:00 ♪ But I've been here before ♪
14:02 ♪ Have I come back for more ♪
14:04 ♪ Another chapter in the history of wrong guys ♪
14:07 ♪ You used to be so meh ♪
14:09 ♪ A limp, lackluster bore ♪
14:11 ♪ But now you're changing into someone I just can't ignore ♪
14:15 - Diva's lament, "Whatever happened to my part?"
14:17 Spam a lot.
14:19 The Lady of the Lake expresses her frustration at the writers.
14:22 ♪ It is one unhappy diva ♪
14:25 ♪ The produce sales have deceived her ♪
14:27 ♪ There is nothing I can sing from my heart ♪
14:32 ♪ Whatever happened to my part ♪
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14:53 Number one, "Getting Married Today," "Company."
14:57 - Pardon me, is everybody there?
14:58 Because if everybody's there,
14:59 I wanna thank you all for coming to the wedding.
15:00 I'd appreciate your going even more.
15:02 I mean, you must have lots of better things to do
15:03 and not a word of it to Paul.
15:04 Remember Paul, you know, the man I'm gonna marry,
15:05 but I'm not because I wouldn't ruin anyone
15:07 as wonderful as he is, but I--
15:08 - This song is the counterpoint
15:09 to this Sondheim show's ambivalent,
15:11 but ultimately hopeful perspective on marriage.
15:13 It's about a bride-to-be getting cold feet
15:16 and the absolute train wreck of anxiety,
15:18 doubt, and self-loathing that follows.
15:20 - Listen, everybody, I'm afraid you didn't hear it.
15:22 Do you wanna see a crazy lady fall apart in front of you?
15:24 It isn't only Paul who may be ruining his life,
15:25 you know, all of us, he's losing our identities.
15:27 I tell him, all my analysts about it,
15:28 and he said to see him Monday,
15:29 but by Monday I'll be floating in the Hudson
15:30 with the other garbage.
15:31 I'm not well, so I'm not getting married.
15:33 - Amy's stream of consciousness is put to frantic music
15:36 at a pace that would tongue-tie the most adept vocalists.
15:39 Also deserving of a mention is "The Ladies Who Lunch,"
15:42 which gets a lot of the glory for its darkly humorous
15:45 and merciless skewering of a certain class of women.
15:48 ♪ The ones who follow the rules ♪
15:52 ♪ And meet themselves at the schools ♪
15:56 ♪ Too busy to know that they're fools ♪
15:59 ♪ I refit your gym ♪
16:03 ♪ I'll drink to them ♪
16:05 - It's "Getting Married Today," however,
16:07 that touches on so many sad and terrifying ideas
16:10 in such a short amount of time that you can't help but laugh.
16:13 By the end of it, Amy is ready to happily submit
16:16 to what she just called a horrifying
16:18 and prehistoric ritual.
16:19 - Let us pray that we are getting married.
16:21 ♪ Amen ♪
16:23 - Do you agree with our picks?
16:30 Check out this other recent clip from Ms. Mojo.
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16:38 (gentle music)
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16:43 (gentle music)
16:45 (upbeat music)