The musical had an industry reading in June 2017. Santino Fontana played the lead role of actor Michael, who transforms into "Dorothy" to obtain a role. Scott Ellis replaced Casey Nicholaw as director. The stage musical version of Tootsie premiered in previews at the Cadillac Palace Theatre in Chicago, beginning September 11, 2018, with an opening at the Palace on September 30, and a run to October 14, 2018. The musical has music and lyrics by David Yazbek with the book by Robert Horn, choreography by Denis Jones, scenic design by David Rockwell, costumes by William Ivey Long, lighting by Donald Holder and direction by Scott Ellis. Santino Fontana stars as Michael Dorsey, with Lilli Cooper as Julie Nichols, Sarah Stiles as Sandy Lester, John Behlmann as Max Van Horn, Andy Grotelueschen as Jeff Slater, Julie Halston as Rita Mallory, Michael McGrath as Stan Fields and Reg Rogers as Ron Carlisle. The Broadway production began previews on March 29, 2019 at the Marquis Theatre and opened on April 23, 2019. The production closed on January 5, 2020, having played 293 regular and 25 preview performances. On May 16, 2019, it was announced that a Non-Equity US national tour will begin in 2020 at Shea’s Buffalo Theatre in New York. It was also announced that a West End production would open the following year. Finally, additional productions were announced for New Zealand, Singapore, Thailand, Hong Kong, Taiwan, and Japan. Exact dates and casts for these productions will be announced in the future.
Characters
Michael Dorsey/Dorothy Michaels - a struggling actor
Julie Nichols - an actress currently starring as Juliet in Juliet's Nurse
Sandy Lester - an out-of-work actress and friend of Michael and Jeff
Jeff Slater - Michael's roommate, an unsuccessful playwright
Max Van Horn - a reality star currently starring as Craig, Romeo's brother, in Juliet's Nurse
Rita Marshall - the producer of Juliet's Nurse
Ron Carlisle - the director and choreographer of Juliet's Nurse
Stan Fields - Michael's agent
Suzie and Stuart - the book writers for Juliet's Nurse
Critic Chris Jones praised the musical in its Chicago premiere for getting many things right, while giving notes for the future Broadway production. In particular, he praised the talent of its lead Santino Fontana. While Michael Phillips commented on the difficulty of translating the early 1980s movie to stage − especially in an era of more gender fluidity – Phillips noted the reviews have ranged "from so-so to very good", while also observing the "opening night laughs were plentiful and the performances savvy". In her review of the Broadway production in Variety, Marilyn Stasio wrote "The new Broadway adaptation of Tootsie is old-fashioned and proud of it — and it’s a surefire crowd-pleaser... this affectionate sendup of a Broadway musical and its uniquely unlikely star. Director Scott Ellis leaves nothing and no one unscathed in staging this satire of a Broadway-bound musical called Juliet’s Nurse...That’s the mixed blessing of Yazbek’s score: the lyrics are so smart, the music can’t always catch up with them... The story holds no surprises for anyone who’s seen the movie, but Horn sprinkles the show’s book with clever one-liners... Well-cast character actors demonstrate their bankable skills at character acting."
Musical numbers
Source: Playbill ;Act I
Overture - Orchestra
"Opening Number" - Ensemble, Michael
"Whaddya Do" - Michael
"What's Gonna Happen" - Sandy
"Whaddya Do" - Michael
"I Won't Let You Down" - Dorothy
"I'm Alive" - Julie, Ron, Max, Dorothy, Ensemble
"There Was John" - Julie, Dorothy
"I Like What She's Doing" - Rita, Julie, Stuart, Suzie, Ron, Max, Dorothy, Ensemble
"Who Are You?" - Michael, Julie
"What's Gonna Happen" - Sandy
"Unstoppable" - Michael/Dorothy
;Act II
Entr'acte - Orchestra
"Jeff Sums It Up" - Jeff, Michael
"Gone, Gone, Gone" - Julie, Female Trio
"Who Are You?" - Julie
"This Thing" - Max
"Whaddya Do" - Jeff, Michael
"The Most Important Night of My Life" - Max, Suzie, Stuart, Rita, Ron, Ensemble