- John Huston as Jake Hannaford, modeled on Ernest Hemingway. Welles denied speculation that the character was also based on himself or Huston, although he noted that there were elements of early Hollywood directors with macho reputations, such as John Ford, Raoul Walsh and William A. Wellman.
- Bob Random as Oscar "John" Dale, the pretty, androgynous leading man of Hannaford's new film, who walked out mid-filming, leaving the picture unfinished.
- Peter Bogdanovich as Brooks Otterlake, a protégé of Hannaford's who is now a commercially successful director in his own right, and who has a talent for mimicking celebrities. The character has many parallels with Bogdanovich himself, who took over the role after the departure of comedian Rich Little (see below).
- Susan Strasberg as Juliette Riche, a savage film critic. The character was a thinly veiled spoof of Pauline Kael, with whom Welles was in a public feud over her allegation (later disproved) that he did not write Citizen Kane. (The role had originally been written with Jeanne Moreau in mind, and was initially played by Bogdanovich's then-wife Polly Platt, who also served as the film's production designer, before eventually being taken over by Strasberg, who reshot the scenes previously filmed with Platt.)
- Oja Kodar as The Actress aka The Red, Red Indian. The unnamed, enigmatic actress features prominently in the film-within-a-film, and is also at Hannaford's party. Much of her role is silent.
- Joseph McBride as Charles Pister, an amalgamation of various cinephiles and socially awkward film critics whom Welles had met over the years. The role was originally played by Bogdanovich, but then re-shot with McBride when Bogdanovich switched to playing Otterlake.
- Lilli Palmer as Zarah Valeska, who owns the ranch which hosts Hannaford's party, was based on Welles's old friend Marlene Dietrich, whom he very much wanted to play the role, but Dietrich was unavailable for filming.
- Edmond O'Brien as Pat, an ageing reactionary actor, and one of Hannaford's cronies.
- Mercedes McCambridge as Maggie Fassbender, a cineaste married to Marvin P. Fassbender, working as Hannaford's Secretary.
- Cameron Mitchell as Zimmer.
- Paul Stewart as Matt Costello, a leading member of "the Hannaford Mafia" of the director's old Hollywood cronies. He is reputed to have a long-standing association with the House Un-American Activities Committee.
- Peter Jason as Marvin P. Fassbender, a bumptious film journalist.
- Tonio Selwart as The Baron, a parody of Welles' former business partner John Houseman, whom he had acrimoniously separated from in the 1940s, and who published several memoirs throughout the 1970s which were scathing of Welles.
- Howard Grossman as Charles Higgam, Hannaford's biographer, a parody of Charles Higham, who had written an influential and unflattering 1970 biography of Welles which had wounded him with its Freudian accusation that he had a "fear of completion" on films. A 1970 Higham article publicising the biography had directly led to one major investor pulling out from The Other Side of the Wind, who was put off by the "fear of completion" charge.
- Geoffrey Land as Max David, a young studio boss and former child actor, spoofing Robert Evans.
- Norman Foster as Billy Boyle, an ageing former child actor from Hannaford's early films, and a member of his entourage, portrayed as a stooge. He is a recovering alcoholic, and a compulsive eater of candy. Foster himself has been seen as something of a Welles stooge, having directed for him in Journey into Fear and one sequence of It's All True.
- Dennis Hopper as Lucas Renard, a young avant-garde director with parallels to Hopper.
- Gregory Sierra as Jack Simon.
- Benny Rubin as Abe Vogel, based on veteran Hollywood agent Abe Lastfogel.
- Cathy Lucas as Mavis Henscher, a spoof of Bogdanovich's then-girlfriend, actress Cybill Shepherd (who was present for at least some of the filming). A young actress, Henscher has difficulty balancing her acting career with the correspondence course her home state makes her take while working.
- Dan Tobin as Dr. Bradley Pease Burroughs, Professor of English Literature at Clivedale Academy, a boys' boarding school in Franahan which had been implicated in a pederasty scandal involving another teacher. His former star pupil is John Dale. When Pease Burroughs is brought out to Hannaford's party to discuss Dale he is noticeably ill-at-ease in the unfamiliar atmosphere of Hollywood.
- George Jessel as Himself
- Richard Wilson as Himself
- Claude Chabrol as Himself
- Curtis Harrington as Himself
- Henry Jaglom as Himself
- Paul Mazursky as Himself
- Other cast members include Stéphane Audran, John Carroll, Cameron Crowe, Allen G. Norman, Pat McMahon, Cameron Mitchell, Robert Aiken and Stafford Repp.
The film features an exceptionally large number of film directors in acting roles in the film, including Claude Chabrol, Norman Foster, Gary Graver, Curtis Harrington, Dennis Hopper, Henry Jaglom and Paul Mazursky, mostly playing Hannaford's entourage of journalists and young film-makers. Other Hollywood celebrities who were friends of Welles were asked to participate, including Jack Nicholson, but were either unavailable or unwilling.
Impressionist Rich Little was originally cast as Brooks Otterlake, but his role was recast part of the way through. There are differing accounts as to the reason for his departure. Welles expressed dissatisfaction with the impressionist's acting ability, and stated that he fired him. Little says that he doesn't know why he lost contact with Welles part of the way through filming. Cinematographer Gary Graver tells a different story: "We shot many, many scenes with him, and he was quite good in each of them...One day, completely out of the blue, Rich showed up with his suitcase in his hand. "Orson," he said, "I haven't seen my wife in a long time. I have to go home." And like that, he was gone!...Orson didn't get angry. He just sat there looking incredulous. He couldn't believe what was happening. The rapport between Orson and Rich had been a good one, so no one had expected Rich's sudden departure." Filming was completed with Bogdanovich playing Otterlake. This necessitated reshooting all of Little's scenes. Little's interpretation of the Otterlake character would have had him using a different accent or impression for every single scene - a device which Joseph McBride thought "uncomfortably labored". By contrast, although Bogdanovich did several impressions in character as Otterlake, he played most of his scenes with his own voice.
Bogdanovich taking over the role of Otterlake meant refilming the scenes featuring Higgam, since Bogdanovich had originally played that (much smaller) role. Bogdanovich played Higgam by doing an impression of Jerry Lewis (at Welles' request), although there is no evidence that Howard Grossman played the role that way when he took over.
The characters played by Foster, Jessel, McCambridge, O'Brien, Stewart and Wilson form Hannaford's entourage, representing the "Old Hollywood"; while Chabrol, Harrington, Hopper, Jaglom and Mazurski play thinly veiled versions of themselves, representing the "New Hollywood." The "Old Hollywood" characters serve as something of a chorus for Hannaford, providing various commentaries on his life.
According to the shooting script, Welles intended to provide the film's short opening narration, intending to dub it in post-production. However, he never recorded it.
Many of the cast and crew worked either for free, or for low wages and/or in exchange for favours from Welles. Huston, a close friend of Welles, worked for the nominal fee of $75,000 - some of which is still owed to his estate, after one of the film's producers embezzled part of the budget (see below). Welles said he could not afford to pay his cinematographer Gary Graver, so instead gave him his 1941 Academy Award statuette for the script of Citizen Kane by way of thanks. Joseph McBride's salary comprised two boxes of cigars. Paul Mazursky recalls that he was never paid for the one night of filming he acted in.
Read more about this topic: The Other Side Of The Wind
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