These things are always self-indulgent and autobiographical, so I would lean into that, à la Martin Short in Fame Becomes Me.
1. "Look At Me" (by Jenifer Lewis, from the immortal Lifetime television film Jackie's Back!) -- I cheat by using "six degrees of separation" and pick a parody opener by a longtime theater stalwart rather than something from an actual show.
2. "Be Italian" (Nine) -- I literally grew up in a highly stereotypical Italian family, it's practically our national anthem.
3. "How Big I'm Gonna Be" (The Original GREASE) -- the last song ever written for Grease (sort of), and an aspirational tune that at least hasn't worn out its welcome like "Corner of the Sky" or "Just Around the Riverbend" or Vitamin C's "Graduation (Friends Forever)."
4. "Pilate's Dream" (Jesus Christ Superstar) -- encountering JCS was my big intro to show biz, and also the choice is a lovely tribute to the late Barry Dennen: charming, mischievous, and a gent to the end. (Probably one of the few earnest moments in the show overall that's actually played straight.)
5. "If I Fell" (Across the Universe) -- my other big self-discoveries at a tender age: a] I might be queer, and b] I am in love with my straight BFF. "Crap!" (Resembles the film's arrangement, but would probably go back to the Fabs' original key just because I don't have Evan Rachel Wood's range. Not strictly a theater song, but eat dirt, it's a movie musical.)
6. Love's Labor's Lost Sequence -- my misadventures in discovering my sexuality and the peaks and valleys of relationships along the way, a monologue incorporating some of my favorites in an unlikely assemblage that includes snatches of "Tonight" from West Side Story, "Easy to Be Hard" from Hair, and "By My Side" from Godspell, among others, chronicling the cycle of first love, cracks in the plaster, and denouement that repeated several times in my life.
7. "Putting It Together" (Sunday in the Park With George) -- chronicling my parallel peaks and valleys as I meet an industry mentor (in the sole instance, to my knowledge, of a teenager meeting an older male online that didn't turn into Chris Hansen fodder) and begin the 16 year long odyssey of making it as a producer (still pending). The book scenes are replaced with vignettes like handling an image rights negotiation for the Michael Jackson Estate and making my first big payday (even though the deal itself fell through), negotiating with a six time Tony nominee over a show in cryogenic stasis due to his insanity, and attempting to work with some of my heroes only to basically not be taken seriously because they first knew me as a teenage fan and I can't shake that image ("everything you do, you still audition" -- why yes, I'll mix and match Barbra and the show lyrics, wouldn't you?).
8. "Holding Out for a Hero" (Footloose) -- as my personal and professional lives go through peaks and valleys, there is one constant: the music of the late Jim Steinman. (This is another drawn-out Sandra Bernhard kind of sequence where I talk about brokering work with the guy, my ongoing attempt to reboot Dance of the Vampires in a fashion resembling its European predecessor, etc.)
9. "Endless Appetite" (Vampire Killers) -- this doubles as a] premiering our new English translation of a song from the piece that may otherwise never be heard due to the mishegas surrounding its rights, and b] a rueful contemplation of everything I've sacrificed along the way in my lust for glory.
10. "I Know Things Now" (Into the Woods) -- in essence, how it feels to be 31, have been through all that, and be a little wiser for the wear, and a little tired of the fight.
Encore: "Where Do You Start" -- that old Bergmans-and-Mandel standard that basically acknowledges, if I'm at the point where I'm actually doing this show, it's the last thing I do trying to make it in this business, and my acknowledgment that it's over, even though I will always love the industry. (Plus, I cheated and didn't technically pick a theater song at the beginning and at the very middle -- it's appropriate to open at the close and do the same at the very end.)
– "Half as Big as Life" from Promises, Promises – "Will He Like Me" from She Loves Me – "I'm Not That Smart" from The 25th Annual Putnam County Spelling Bee – "The God-Why-Don't-You-Love-Me Blues" from Follies – "Natasha" from A Day in Hollywood / A Night in the Ukraine – "Something to Live For" from Sophisticated Ladies – "Uyamemeza Ungoma" from Sarafina! – "The Lynching Blues" from Bring in 'da Noise, Bring in 'da Funk – "Blues in the Night" from Swing! – "Promises, Promises" from Promises, Promises