PLAYBILL PLAYLIST: Billy Porter, Annaleigh Ashford, Will Van Dyke and Friends Pick Songs to Deal With a Break-Up

Playlist   PLAYBILL PLAYLIST: Billy Porter, Annaleigh Ashford, Will Van Dyke and Friends Pick Songs to Deal With a Break-Up
Will Van Dyke and Friends, a concert featuring the music of Will Van Dyke and spotlighting his new musical Writing Kevin Taylor — about breaking up and trying to get back together — will be held Oct. 14 at 54 Below. In anticipation of the evening, the cast picks their favorite break-up songs as part of's Playbill Playlist.

Billy Porter
Billy Porter Photo by Joseph Marzullo/WENN

The 9:30 PM concert will feature Kinky Boots Tony Award winner Billy Porter, Tony nominee Annaleigh Ashford (Kinky Boot), Brandon Victor Dixon (Motown), Tamika Lawrence (Matilda, The Book of Mormon), Mike Wartella (Wicked), Jason Gotay (Bring It On), Randy Blair, Matt Doyle (The Book of Mormon, War Horse), Katie Gassert, Preston Sadleir (Next to Normal), David Josefsberg (The Wedding Singer), Brad Weinstock and Sally Wilfert (Assassins).

The concert promises songs written by Van Dyke in collaboration with Rick Elice and Matt Doyle, selections from the his 2010 recording "Chasing the Day: The Music of Will Van Dyke" and tunes from his newest recording "Writing Kevin Taylor."

A concept album set for digital release Oct. 15, Writing Kevin Taylor has music and lyrics by Van Dyke, with book and lyrics by Josh Halloway. Writing Kevin Taylor is described as "a three-person musical comedy about the unlikely friendships and unexpected moments that bring us together. It's a show about how much you can get out of life, when you let someone in."

"The premise of [Writing Kevin Taylor] is simple," composer Van Dyke explained to "Wife leaves Writer. Writer hires Boy. Boy pretends to be Writer's estranged son to help win back Wife. Things get interesting. It's a musical comedy about the unlikely friendships and unexpected moments that bring us together. Since the inciting incident of the whole show is a break up, we thought it would be fun to share our favorite break up songs with you!"

"Writing Kevin Taylor," which will be on sale at 54 Below, features Ben Crawford, Lisa Howard and Preston Sadleir and is produced by Derik Lee and Van Dyke. "Writing Kevin Taylor" has arrangements and orchestrations by Van Dyke, with additional orchestrations by August Eriksmoen and Brian Usifer. The band features Alec Berlin (guitar), Steve Gilewsi (bass), Mason Ingram (drums), Allison Seidner (cello), Hiroko Taguchi (violin) and Van Dyke (piano). Will Van Dyke and Friends is directed by DB Bonds and will be performed by an eight-piece band led by Van Dyke at the piano.

Van Dyke also served as musical director for the Off-Broadway revival of Rent and in the orchestra for The Addams Family. For more on the composer and his work, read's Contemporary Musical Theatre Songwriters You Should Know.

54 Below is located at 254 W. 54 Street. Tickets are $25 and $35 (plus a $25 food/drink minimum). For more information and tickets, call (866) 468-7619 or visit

Will Van Dyke: "Torch" by Alanis Morissette. It is, of course, off her lesser-known "Flavors of Entanglement" album that I love and adore. It's just a song about the hurt of missing another person and the things about them that made you feel safe. She just opens a vein and lets it all out. It is pretty incredible.

Billy Porter: Here are the first Top 10 off the top of my head… In other words, you can't just choose ONE. I won't do it!!! 1. "I Love You More Than You'll Ever Know" (Donny Hathaway) 2. "Congratulations" (Vesta Williams) 3. "I've Learned To Let Things Go" (John Bucchino) 4. "Still Hurting" (Jason Robert Brown) 5. "My Man" (Fanny Brice) 6. "Not A Day Goes By" (Stephen Sondheim) 7. "Superstar" (Hal David/Burt Bacharach) 8. "I Have Nothing" (Whitney Houston) 9. "Lush Life" (Billy Strayhorn) 10. "How Do You Keep The Music Playing" (Michael Legrand/Alan and Marilyn Bergman).

Jason Gotay: "Let Me Leave" (Marc Broussard). Not only are the lyrics and music absolutely heartbreaking, but Marc Broussard's voice is so truthful and honest. There's a raw quality to his delivery that gives me chills! Get into him!

Jason Gotay: "Merry Happy" (Kate Nash). I love this song because it talks about breakups in a more positive way. "Yeah, you made me merry, made me very, very happy, but you obviously didn't wanna stick I learned from you." If we could look at breakups from THAT perspective, things would be infinitely simpler. Easier said than done, I know.

Jason Gotay: "If You Only Knew" (Will Van Dyke). Not just saying this, but this has been one of my favorite "new musical theatre songs" for years. So haunting and beautiful, and Morgan James' rendition is so soulful! Makes my heart hurt!

Randy Blair: "Dog Days Are Over" (Florence + The Machine). Aww, I've been there. If you're looking to shake off those post-break up emo feels with a private, semi-nude session of jumping up and down on the bed, I recommend the hipstery healing powers of Florence and the Machine's "Dog Days Are Over." I can guarantee you'll feel mighty, in control and slightly Wiccan. Don't let anyone see you do this though, unless your roommate is Tilda Swinton.

Randy Blair: "I Can't Make You Love Me" (Bonnie Raitt). If you need to wallow in self pity, listen to Bonnie Raitt's "I Can't Make You Love Me" while eating an entire pint of Ben & Jerry's Peach Cobbler. It's their worst and least purchased flavor and the only thing more unloveable than you.

Randy Blair: "No Children" (The Mountain Goats). But seriously, the best bad relationship song is hands down "No Children" by The Mountain Goats. So depressing that it's funny, beautiful and wrist-slitting simultaneously, I can already hear you belting out a rousing chorus of "I hope you die! I hope we both die!"

Preston Sadleir: "The Absence of Your Company" (Kim Richey). Hands down, I'd say "The Absence of Your Company" by Kim Richey. So beautiful, and the lyrics really speak to how difficult it is to walk away from someone who doesn't love you back — oof, heart pains. Plus, I've got a bangarang harmony I do with it in the car: Car-mony!

Tamika Sonja Lawrence: "Can We Pretend" (Bill Withers). My favorite break-up song of all time is "Can We Pretend" by Bill Withers. It's so gut wrenching and personifies the first thought many of us have after heartbreak: "I wish I would have never let you into my heart."

Tamika Sonja Lawrence: "Just Ain't Gonna Work Out" (Mayer Hawthorne). My second favorite break up song is "Just Ain't Gonna Work Out" by Mayer Hawthorne. It's a sensibly fun song to add to your "good riddance" soundtrack when you're telling some loser "happy trails."

Brad Weinstock: "F*ck You" (Cee Lo Green). The title says it all. A sentiment everyone can relate to, and the audible joy Cee Lo gets in relaying this message is contagious. You'll feel better by the end of those four minutes.

Brad Weinstock: "Sensitive Song" from Cops: The Musical. If you don't know this one, you should definitely YouTube it. Like many a great break-up song, it starts off sweetly, praising the girl in question. Then, about 30 seconds in, it takes a sharp U-turn with a chorus that is hilarious, catchy as hell and probably too obscene to print here.

Brad Weinstock: "You Oughta Know" (Alanis Morissette). Beyond the legends of this song being about Dave Coulier ("Cut-It-Out"), this song is a sucker punch. Who hasn't rocked out in their car or shower to this one after a painful break-up?

Sally Wilfert: "Why" (Annie Lenox). The lyric perfectly describes two people ending their relationship. Realizing that no matter how much they wish and hope and try… the ship is sinking. It is the perfect musical setting of the word "WHY" — a question asked in this situation from the depths of one's soul. And yes, I've been there.

Mike Wartella: "Fix You" (Coldplay). I always seem to listen to "Fix You," which I feel like will probably pop up more than once on this list. It's just devastating. Also, I'm kinda lame, but "See I'm Smiling" from The Last Five Years, definitely gave me some catharsis after my divorce.

Katie Gassert: So, for me, there are definitely three stages of break-up songs. There's the: "I want to cry with Joni Mitchell to 'Both Sides Now.'" Then there's the: "What am I doing with my life, and can Alanis [Morissette] help me with 'Incomplete'?" phase. But then I always end with the: "You know what, I don't need him or anyone with Blaque's 'I'm Good'," which you may or may not remember from the credits of one of my favorite movies, "Honey." That's how I deal.

Annaleigh Ashford: "It's Too Late" (Carole King). It's so positive! She literally says, "Still I'm glad for what we had, and how I once loved you." The sound of the song isn't sad and pitiful like other break-up songs that make you want to cry and eat too much ice cream and wear clothes too many days in a row. It's got a cool drum part and makes you want to dance in a smooth 70s kind of way. There is also a sensible saxophone solo.
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