In Tootsie (1982), Hoffman portrays Michael Dorsey, a struggling actor who finds himself dressing up as a woman to land a role on a soap opera.
His co-star was Jessica Lange.
Tootsie earned ten Academy Award nominations, including Hoffman's fifth nomination.

Under direction by Sydney Pollack, Hoffman's role demanded "a steady bombardment of opposites—edgy then funny, romantic then realistic, soft then quivering."
To film critic David Denby, Hoffman's character "embodies vulnerability and drive in perfect proportion.
He has the knack of making everything he does seem perilous, and so audiences feel protective of him and root for him."
Hoffman's acting was made more difficult than necessary, however, as he was not given the rehearsal time Pollack promised:
I like to be very prepared, and I feel that the success or failure of a film is many times determined before you start principal photography.
I wanted rehearsal very much.
I was promised two weeks and was grieved that I didn't get it.
We also followed the risky course of starting to shoot with a screenplay that wasn't completed.

Fellow actor Gary Oldman reported that, during a telephone conversation with Hoffman, the latter recalled having made comments toward a "very powerful" industry figure who ensured that he was unable to find work in Hollywood for some time following Tootsie.
In 1983, Hoffman became a Major Donor for The Mirror Theater Ltd, alongside Paul Newman and Al Pacino, matching a grant from Laurance Rockefeller.
The men were inspired to invest by their connection with Lee Strasberg, as Lee's then daughter-in-law Sabra Jones was the Founder and Producing Artistic Director of The Mirror.

In 1984, Hoffman starred as Willy Loman in the Broadway revival of Arthur Miller's play Death of a Salesman.
He reprised his role in a TV movie of the same name, for which he won the 1985 Emmy Award for Outstanding Lead Actor along with a Golden Globe.

Hoffman first read the play at the age of 16, but today considers the story much like his own: "It was a blueprint of my family.
I was the loser, the flunky, and my brother, a high-school varsity football player, was Biff."
Author Marie Brenner notes that Hoffman "has been obsessed with the play" throughout his career: "For years he has wanted to be Willy Loman; when he discovered that Arthur Miller was his neighbor in Connecticut, they began to talk about it in earnest."
For Hoffman, the story also left a deep emotional impact from the time he first read it:
I read that play, and I was just destroyed by it.
It was like finding out something terrible about my family.
I just shook.
I felt like my family's privacy had been invaded.
I couldn't even talk about it for weeks.

Hoffman rehearsed for three weeks with the play's original star, Lee J. Cobb, and remembers seeing his stage performance: "I'll never forget that period in my life.
It was so vivid, so intense, watching Lee J. Cobb and his sixteen-inch guns as Willy.
God, how I think about what I saw on that stage!"
Brenner adds that Hoffman "has been training like a boxer for the role that so exhausted Cobb he had to be replaced after four months."
The original play was directed by Elia Kazan, who Hoffman considers "the perfect director, the best there ever was. . . .
God, I would have done anything to have worked with Kazan."

Hoffman's worst film failure was Elaine May's Ishtar (1987), co-starring Warren Beatty, who also produced it.
Hoffman and Beatty play two down-and-out singer-songwriters who travel to Morocco for a nightclub gig and get caught up in foreign intrigue.
Much of the movie was filmed in Africa.
The film faced severe production problems, mostly related to its $55 million cost, and received overwhelmingly negative reviews.
However, Hoffman and Beatty liked the film's final cut and tried to defend it.
Hoffman and Beatty were unaffected by the flop, and Ishtar became a cult film.
Quentin Tarantino, for one, has called it one of his favorite movies, partly due to the humorous lyrics of the songs written by Paul Williams.
Hoffman describes why he loves the film:
The
In Tootsie (1982), Hoffman portrays Michael Dorsey, a struggling actor who finds himself dressing up as a woman to land a role on a soap opera. His co-star was Jessica Lange. Tootsie earned ten Academy Award nominations, including Hoffman's fifth nomination.
Under direction by Sydney Pollack, Hoffman's role demanded "a steady bombardment of opposites—edgy then funny, romantic then realistic, soft then quivering." To film critic David Denby, Hoffman's character "embodies vulnerability and drive in perfect proportion. He has the knack of making everything he does seem perilous, and so audiences feel protective of him and root for him." Hoffman's acting was made more difficult than necessary, however, as he was not given the rehearsal time Pollack promised:
I like to be very prepared, and I feel that the success or failure of a film is many times determined before you start principal photography. I wanted rehearsal very much. I was promised two weeks and was grieved that I didn't get it. We also followed the risky course of starting to shoot with a screenplay that wasn't completed.
Fellow actor Gary Oldman reported that, during a telephone conversation with Hoffman, the latter recalled having made comments toward a "very powerful" industry figure who ensured that he was unable to find work in Hollywood for some time following Tootsie. In 1983, Hoffman became a Major Donor for The Mirror Theater Ltd, alongside Paul Newman and Al Pacino, matching a grant from Laurance Rockefeller. The men were inspired to invest by their connection with Lee Strasberg, as Lee's then daughter-in-law Sabra Jones was the Founder and Producing Artistic Director of The Mirror.
In 1984, Hoffman starred as Willy Loman in the Broadway revival of Arthur Miller's play Death of a Salesman. He reprised his role in a TV movie of the same name, for which he won the 1985 Emmy Award for Outstanding Lead Actor along with a Golden Globe.
Hoffman first read the play at the age of 16, but today considers the story much like his own: "It was a blueprint of my family. I was the loser, the flunky, and my brother, a high-school varsity football player, was Biff." Author Marie Brenner notes that Hoffman "has been obsessed with the play" throughout his career: "For years he has wanted to be Willy Loman; when he discovered that Arthur Miller was his neighbor in Connecticut, they began to talk about it in earnest." For Hoffman, the story also left a deep emotional impact from the time he first read it:
I read that play, and I was just destroyed by it. It was like finding out something terrible about my family. I just shook. I felt like my family's privacy had been invaded. I couldn't even talk about it for weeks.
Hoffman rehearsed for three weeks with the play's original star, Lee J. Cobb, and remembers seeing his stage performance: "I'll never forget that period in my life. It was so vivid, so intense, watching Lee J. Cobb and his sixteen-inch guns as Willy. God, how I think about what I saw on that stage!" Brenner adds that Hoffman "has been training like a boxer for the role that so exhausted Cobb he had to be replaced after four months." The original play was directed by Elia Kazan, who Hoffman considers "the perfect director, the best there ever was. . . . God, I would have done anything to have worked with Kazan."
Hoffman's worst film failure was Elaine May's Ishtar (1987), co-starring Warren Beatty, who also produced it. Hoffman and Beatty play two down-and-out singer-songwriters who travel to Morocco for a nightclub gig and get caught up in foreign intrigue. Much of the movie was filmed in Africa. The film faced severe production problems, mostly related to its $55 million cost, and received overwhelmingly negative reviews. However, Hoffman and Beatty liked the film's final cut and tried to defend it. Hoffman and Beatty were unaffected by the flop, and Ishtar became a cult film. Quentin Tarantino, for one, has called it one of his favorite movies, partly due to the humorous lyrics of the songs written by Paul Williams. Hoffman describes why he loves the film:
The
Dustin Hoffman