One of the great things about theatre songs is how they tell the stories of people's lives and can echo our own feelings. Certainly, joyous occasions often call for the exuberance of a big Broadway number, but when we're experiencing the end of a relationship, musicals can also offer us comfort and even a kind of pick-me-up by way of their tales of love and loss. Sometimes it's soothing to listen to (or sing) a showtune about a character feeling sad the way you are. It may even help you through anger and all the other classic stages of grief to the point where you're (to quote the master himself) "moving on."
Click through to read my selections for the Top Ten Broadway Break-Up Songs.
10. "There's A Fine, Fine Line" from Avenue Q
As in any story about young people finding themselves, there is a lot of soul-searching and flip-flopping among the characters (human and monster) in Avenue Q. It's all well and good to be experimenting with different behaviors and career paths as you make your way in the world, but sometimes the people that love you become collateral damage. That's exactly what happens to Kate Monster when she gets rejected by the guy she's just started dating and falling for, Princeton. This simple and sweet song shores up her conviction to move forward with her own life. No matter how down in the dumps you may be, it's hard not to charge your batteries from singing along.
9. "Never" from On The Twentieth Century
"Never" is not so much a break-up song because at the start of On The Twentieth Century, Lily Garland and Oscar Jaffe have already long ago broken up. When Oscar's associates beg Lily to help him out of a career sinkhole, Lily responds with this hilarious tirade of Comden and Green's witty words and Cy Coleman's zesty music, extolling her determination to stay away from Oscar. If you're longing for someone who you know is bad for you, this might help you let it go, or at least have a laugh while trying. I cannot wait to hear what Broadway's peerless coloratura clown, Kristin Chenoweth, does with it in the forthcoming revival.
8. "Under Separate Cover" from A Class Act
Musical theatre fans around the world have long celebrated Ed Kleban's Pulitzer prize-winning lyrics for A Chorus Line. 2001's A Class Act brought his music to the mainstem as well, and an irresistible treasure of this bio musical was Kleban's heartbreaking "Under Separate Cover." The song was theatricalized as a trio between Ed, his soon-to-be ex-girlfriend Sophie and, in bookwriter-director [and star] Lonny Price's meta concept, a singer he's working with, who winds up being his next relationship. The pulsing accompaniment brings to life the urgency of romantic tension and lyrics offer introspective realness as the melody climaxes with excitement.
7. "Many A New Day" from Oklahoma!
From the beginning of Oklahoma!, it's pretty clear to the audience Curly and Laurey are made for each other, although they may be the last to know. At one point in their cat-and-mouse game of playing it cool, Curly flirts with another girl in front of Laurey, provoking this ode to independence. Laurey is, for her time and place, an empowered, intelligent woman, and Oscar Hammerstein II's lyrics illustrate confidence and spunk beyond the typical ingénue. It's a good song for picking your head up and doing your own thing.
6. "Could I Leave You?" from Follies
Leave it to Stephen Sondheim to write the most complicated of the Broadway break-up songs. In Follies, Phyllis does not, in fact, actually leave Ben, although the audience may believe it's possible when she sings the song. Phyllis herself may even believe it. That's part of the power of this piece. Jan Maxwell's performance in the recent revival was a powerful exploration of all the contradictory layers of feelings intense relationships bring. At first glance, this incisive lyric has always had angry flair, but Maxwell brought incredible vulnerability and seemed to really be asking herself whether she could leave. If you're going through a rough spot and the average showtune seems superficial, try this one on for size.
5. "Be On Your Own" from Nine
Maury Yeston's thrilling break-up anthem, "Be On Your Own" from Nine, manages an impressive feat. The song so clearly comes from a sad place and yet rides a wave of steely anger so theatrical it's almost operatic. Karen Akers's rich rendition left a permanent mark in Broadway history with its profound pathos, and it's hard to imagine anyone ever being as moving or as musical in the role. It's still a killer song to sing for anyone breaking up or performing for someone who is. Betty Buckley is, of course, nearly apocalyptic in her version on "The Maury Yeston Songbook," and Ann Crumb's recording from the London concert of Nine is packed with pop opera power.
4. "Tell Me On A Sunday" from Song And Dance
Andrew Lloyd Webber's Song And Dance and Tell Me On A Sunday, the original song cycle that formed Act One of the show, can sometimes get lost in the shuffle of the composer's major works nowadays. Nonetheless, the song, "Tell Me On A Sunday" has endured as a Broadway standard for decades now. Decidedly in the sad category of break-up songs, "Tell Me On A Sunday" doesn't even protest the end of the relationship. With complete humility, it just asks that the end come in a slightly easier way — on a Sunday, maybe in a park or zoo. If you go there with this song, it's pretty weepy, but sometimes that's just what you need.
3. "We Do Not Belong Together" from Sunday In The Park With George
Speaking of Sundays in the park, Dot in Sunday In The Park With George, sings what is essentially the 11 o'clock number of the first act, "We Do Not Belong Together" confirming the end of her relationship with George, something he has barely even acknowledged. Of course, this lack of attention from him is the reason they're breaking up and is expressed musically and lyrically with poetry and power and personality as only Sondheim can. This is one of the greats, but even better than great when voiced by original Dot, Bernadette Peters, who should have won the 1984 Tony even for just this one number alone. She'll take you from the disappointment through to the turning of the page with a voice that yearns and aches with tremendous humanity.
2. "Wherever He Ain't" from Mack & Mabel
When you first break up, you may not be ready for "Wherever He Ain't." If you're still holding on to all your feelings of love, this song may be Level Two for you. But once you get there, this is your jam. Another Bernadette Peters original cast album gem, her vim and verve and piss and vinegar and booming belt voice bring to life all Jerry Herman's delicious hyperbole about just how much Mabel wants to get away from Mack. It's sort of like Beyoncé's "Invincible" for the Keystone Cop set.
1. "Goodbye Until Tomorrow/I Could Never Rescue You" from The Last Five Years
Our number one Broadway Break-Up song is a cheat in several ways. First of all, it's not from Broadway as Jason Robert Brown's seminal cult hit The Last Five Years, has never played Broadway. We will, however, look past that, since when it inevitably does get to Broadway, it will no doubt be considered a revival — and because the rapturous film adaptation (starring the duly perfect Anna Kendrick and Jeremy Jordan) opens in theatres and on demand Feb. 13. The Last Five Years will certainly be on Broadway fans' minds come Valentine's Day! Also, though, "Goodbye Until Tomorrow" is not totally a break-up song because the two characters exist in opposite chronologies, so this song the end of the show is Jamie breaking up with Cathy while she is first getting together with him! Maybe that's what makes it so moving, though. Of course the pain of a break-up is precisely that memory of the beginning of the relationship, the longing for what used to be. Brown's melancholy undertow pulls the two songs together inextricably and can reach your broken heart when possibly no other song could.
(Ben Rimalower is the author and original star of the critically acclaimed Patti Issues, currently on a worldwide tour. His new solo play, Bad with Money, performs through April 29 at The Duplex in NYC. Read Playbill's coverage of the show here. Visit him at benrimalower.com and follow @benrimalower on Twitter.)