|Written by||Warren Leight|
|Date premiered||March 11, 1998|
|Place premiered||East 13th Street Theater
New York City
|Setting||New York City, 1985-1953|
Side Man is a memory play by Warren Leight. His inspiration was his father Donald, who worked as a sideman, in jazz parlance a musician for hire who can blend in with the band or star as a solo performer, according to what is required by the gig.
The play's narrator is Clifford Glimmer, the only son of Gene, a talented but self-absorbed jazz trumpeter, and his alcoholic wife Terry, who describes the tumultuous relationship his parents shared and the haphazard career journey Gene followed over the course of three decades. Dedicated more to his music than his family, he refuses to accept a regular job to support them, and their home life gradually unravels, with Clifford eventually assuming the role of breadwinner his father has forsaken and offering his mother the emotional support Gene cannot. Scenes alternate between the family's Spartan New York City apartment and the smoke-filled nightclubs and cabarets of another era.
Directed by Michael Mayer, the play premiered on March 11, 1998 at the off-off-Broadway East 13th Street Theater, where it ran until March 29. The cast included Frank Wood as Gene, Robert Sella as Clifford, and Edie Falco as Terry. Joseph Lyle Taylor as AL, Michael Mastro as Ziggy, Kevin Geer as Jonsey and Angelica Torn as Patsy.  After 27 previews, the Broadway production, also directed by Mayer, opened on June 25, 1998 at the Criterion Center Stage Right. It later transferred to the John Golden Theatre for a total run of 517 performances. Wood and Sella reprised their roles, with Wendy Makkena replacing Falco as Terry. Later in the run Sella was replaced successively by Andrew McCarthy, Christian Slater, and Scott Wolf, Wood was replaced by Michael O'Keefe, and Makkena was replaced by Falco.
In reviewing the off-Broadway production, Peter Marks of the New York Times called it "both heartbreaking and touching, a play of true feeling, full of affection for its characters and insight about the events it conjures." 
Through an arrangement with Actors' Equity, which allowed for the British cast of The Real Thing to travel to Broadway, Side Man, with Wood, Falco, and Jason Priestley, opened on February 8, 2000 in London's West End at the Apollo Theatre, where it ran for slightly more than two months.
Awards and nominations
- 1999 Tony Award for Best Play (winner)
- 1999 Pulitzer Prize for Drama (nominee)
- 1998 Drama Desk Award for Outstanding New Play (nominee)
- 1998 Outer Critics Circle Award for Outstanding New Play (nominee)
Music featured in the play
- 1. I Remember Clifford [7:12]
- 2. Rockin' Chair [3:08]
- 3. I Don't Stand A Ghost Of A Chance [7:25]
- 4. Daahoud [4:07]
- 5. Cristo Redentor [5:47]
- 6. Land's End [5:02]
- 7. Chelsea Bridge [3:27]
- 8. A Night In Tunisia [11:07]
- 9. Time [5:07]
- 10. It Never Entered My Mind [4:02]
RCA Victor released a CD compiled from the original recordings.