1974–1988: Breakthrough and stardom
After some television-commercial and radio appearances (including on CBS Radio Mystery Theater in 1974); Patinkin started his career on the New York stage in 1975, starring in Trelawny of the 'Wells' as Arthur Gower. Patinkin starred alongside Meryl Streep, who played Imogen Parrott, and John Lithgow, who played Ferdinand Gadd. Clive Barnes of The New York Times praised the production writing, "The production looks beautiful and, indeed, still charms". From 1975 through 1976, Patinkin played the Player King and Fortinbras, Prince of Norway in a Broadway revival of Hamlet, with Sam Waterston in the leading role. In 1977 he starred in the play The Shadow Box written by Michael Cristofer. He had his first film role as a Pool Man in the political comedy The Big Fix (1978) starring Richard Dreyfus, John Lithgow, and F. Murray Abraham. The following year he acted in the coming of age romantic comedy French Postcards and the neo-noir Last Embrace.
Patinkin had his first success in musical theater when he starred as Che in Andrew Lloyd Webber's Evita, opposite Patti LuPone, on Broadway in 1979. Walter Kerr of The New York Times described his performance as "vigorous". James Lardner of The Washington Post wrote, "Patinkin gives a sympathetic, consistent and rather sweet performance". Patinkin won the Tony Award for Best Featured Actor in a Musical for his performance. He also received a nomination for the Drama Desk Award for Outstanding Actor in a Musical. Patinkin took film roles in Milos Forman's historical drama Ragtime (1980) playing Tateh and Sidney Lumet's drama Daniel (1983) portraying Paul Isaacson.
Patinkin won acclaim for his role as an Orthodox Jewish man Avigdor in Barbra Streisand's romantic drama epic Yentl (1983), which earned him a nomination for the Golden Globe Award for Best Actor – Motion Picture Musical or Comedy. Richard Corliss of Time praised his performance but criticized Streisand's choice to not have him sing in the film. Corliss wrote, "For her male co-star she hired Mandy Patinkin, who has wrapped his crystalline Broadway tenor voice around Stephen Sondheim and Andrew Lloyd Webber, then gave him no songs to sing". Veron Scott of United Press International wrote, "When Patinkin is in a scene it is difficult to focus on anyone else, including Streisand who is at her very best in Yentl. He plays profound, passionate men of action." Patinkin noted that both Ragtime (1981) and Daniel (1983) weren't as successful as he had hoped commercially and critically saying, "When you care about the content of a film, you want people to see it". He stated he had a positive experience working with Streisand saying, "'She tried to overcome her superstardom to make me feel comfortable. She worked hard to get to know me for what I am." Patinkin also was able to explore his Jewish roots while making the film saying, "I also spent a couple of weeks in Ohr Semach in Jerusalem at a yeshiva, studying the Talmud and attending lectures. The experience awakened many thoughts and feelings that had been sleeping in me for some time."
Patinkin returned to Broadway to star in Stephen Sondheim and James Lapine's Pulitzer Prize-winning musical Sunday in the Park with George, in which he played the pointillist artist Georges Seurat and his fictional great-grandson George. Performances began in April 1984 and he starred opposite Bernadette Peters. Patinkin earned nominations for a Tony Award for Best Actor in a Musical and a Drama Desk Award for Outstanding Actor in a Musical. Frank Rich of The New York Times wrote, "Seurat, here embodied commandingly by Mandy Patinkin, could well be a stand-in for Mr. Sondheim, who brings the same fierce, methodical intellectual precision to musical and verbal composition that the artist brought to his pictorial realm." Patinkin left the show on September 17 and was replaced by Robert Westenberg. He returned to the show on August 5, 1985, until the show closed two months later. His performance was captured on film and shown on television as a part of American Playhouse. The following year he took the role of Buddy Plummer in Follies: In Concert at Lincoln Center.
In 1985 Patinkin took a leading role in the romantic fantasy comedy Maxie opposite Glenn Close. Variety gave the film a mixed review but praised Patinkin, writing, "Much of the credit for keeping [Maxie] alive must go to Mandy Patinkin, who shows himself to be a good-looking leading man with a rare light touch for romantic comedy." In 1987, Patinkin played Inigo Montoya in Rob Reiner's The Princess Bride, playing the role of the best swordsman in the country, looking to avenge his father's death. Patinkin acted opposite Cary Elwes, Robin Wright, Andre the Giant, and Billy Crystal. Variety praised his performance writing, "Patinkin especially is a joy to watch and the film comes to life when his longhaired, scruffy cavalier is on screen." His character has earned a cult following and his memorable line "My name is Inigo Montoya. You killed my father. Prepare to die," was ranked as one of IGN's best movie moments.
The following year in 1988 he acted in the science fiction action film Alien Nation directed by Graham Baker and the neo-noir film The House on Carroll Street directed by Peter Yates.