- 2005: Played Special Agent Jason Gideon in the CBS crime drama "Criminal Minds"; left series due to creative differences
- 2003: Cast as Rube Sofer in the Showtime comedy-drama "Dead Like Me"
- 2001: Cast as producer Joseph Papp in the film biography "Pinero"
- 2000: Co-starred on Broadway alongside Toni Collette and Eartha Kitt in "The Wild Party"; earned Tony nomination as Lead Actor in a Musical
- 2000: Provided a character voice for the English-language version of Hiyao Miyazaki's anime "Laputa: Castle in the Sky"; screened at the New York International Children's Film Festival
- 1999: Co-starred as the media savvy political advisor Kenneth Duberstein in the acclaimed Showtime drama "Strange Justice"
- 1999: Resumed role of Dr Jeffrey Geiger on "Chicago Hope" on a recurring basis
- 1999: Played the comic villain in the children's film "The Adventures of Elmo in Grouchland"; also sang and danced
- 1998: Had supporting role in "Lulu on the Bridge"; screened at Cannes; released direct-to-video in 1999
- 1998: Cast as an obnoxious American tourist in John Sayles' Spanish-language "Men With Guns"
- 1998: Returned to Broadway in "Mandy Patinkin in Concert: Mamaloshen", drawing material from his album of Yiddish songs
- 1997: Had title role in the TNT production of "The Hunchback"
- 1996: Starred in the PBS production of Arthur Miller's "Broken Glass"
- 1995: Made guest appearance as himself on the HBO comedy "The Larry Sanders Show"
- 1995: Asked to be released from "Chicago Hope" citing a desire to spend more time with family; agreed to make occasional guest appearances
- 1994: TV series debut, part of the ensemble for the ambitious CBS medical drama, "Chicago Hope"
- 1993: Replaced Michael Rupert in the Broadway musical "Falsettos", directed by Lapine
- 1993: Made cameo appearance in Lapine's film comedy "Life with Mikey"
- 1993: Co-starred in Philip Haas' "The Music of Chance"
- 1991: Portrayed Alfred de Musset in Lapine's feature directorial debut "Impromptu"
- 1991: Returned to Broadway playing Archibald Craven in the musical version of "The Secret Garden"
- 1990: Feature singing debut, "Dick Tracy"; songs written by Stephen Sondheim; played small role of piano player 88 Keys for Breathless Mahoney (Madonna)
- 1990: Feature singing debut, "Dick Tracy"; songs written by Stephen Sondheim; played small role of piano player for Breathless Mahoney (Madonna)
- 1989: Broadway concert debut, "Mandy Patinkin in Concert--Dress Casual"
- 1989: Appeared as Leontes in a NYSF staging of "The Winter's Tale", directed by James Lapine
- 1989: Began performing a weekly concert series Off-Broadway at the Public Theater
- 1988: Co-starred as a being from another planet in "Alien Nation"
- 1987: Undertook controversial role of a transsexual in the Nick Bicat-David Hare musical "The Knife", produced at the New York Shakespeare Festival
- 1987: Breakthrough film role, Inigo Montoya in Rob Reiner's "The Princess Bride"
- 1987: Breakthrough film role, Inigo Montoya in Rob Reiner's "The Princess Bride"
- 1985: Played role of Buddy in "Follies in Concert", a staging of the Stephen Sondheim-James Goldman musical; recorded and filmed for airing on PBS
- 1985: Co-starred with Glenn Close in the feature "Maxie"
- 1985: Fired from "Heartburn" and replaced by Jack Nicholson (July)
- 1984: First collaboration with Stephen Sondheim, "Sunday in the Park With George"; directed by James Lapine; earned Tony nomination as Lead Actor in a Musical; filmed for TV and aired on PBS in 1986
- 1983: Offered a fine turn as the romantic lead opposite Barbra Streisand in "Yentl"
- 1981: Cast as Tateh, the future filmmaker, in "Ragtime"
- 1981: Returned to the stage to play Hotspur in NYSF Central Park production of "Henry V"
- 1979: Made guest appearance on the classic sitcom "Taxi"
- 1979: Breakthrough stage role, Che in "Evita"; won 1980 Tony Award as Featured Actor in a Musical
- 1979: TV-movie debut "Charleston" (NBC)
- 1978: Appeared opposite Dianne Wiest in the New York Shakespeare Festival production of "Leave It to Beaver Is Dead" production
- 1976: Originated the role of Mark, the lover of a man dying of cancer, in "The Shadow Box" at Long Wharf Theater; reprised role in 1977 Broadway production
- 1975: Broadway debut in "Trelawny of the Wells" alongside Meryl Streep, Mary Beth Hurt, John Lithgow and Michael Tucker
- 1962: Began singing at age nine in the choir at his temple on the South Side of Chicago (date approximate)
- Dropped out of Juilliard; worked briefly in children's theater in Baltimore; gained Equity card
- Was signed to play Che in film version of "Evita" to be directed by Oliver Stone and to star Meryl Streep; Streep withdrew from project in late 1989 and project was delayed
- During run of "The Shadow Box", co-star Geraldine Fitzgerald gifted him with singing lessons
- Turned down the lead in the original London production of "The Phantom of the Opera" because he didn't want to move his family
- Toured frequently performing one-person concerts




