Woody Allen plays Alvy Singer. It's worth noting that this is the first time Allen plays a sort of normal person in one of his own films. His early comic persona was gone, replaced by something with a few more dimensions. He is also a very unlikely leading man at this time. Comic foil - yes. But he’s not the usual Robert Redford type.

Diane Keaton plays Annie Hall. Huge parts of Annie was based on Keaton. It was Keaton's own fashion style that was used in the film (and we still see around today). Her real surname is Hall. She was a night club singer. We also see a more romantic, vulnerable performance from her, one that would earn her the Academy Award for Best Actress. Kay Lenz was apparently considered for the role, but it is hard to imagine anyone but Keaton playing Annie.

Like Allen, she tends not to watch herself. She did see Annie Hall though. Says Keaton[7]:

“I thought it worked emotionally. I was surprised that in the end, I felt something when we said goodbye.”

Tony Roberts plays Rob, in his first appearance in an Allen film. Roberts and Allen were good friends, having met during Don't Drink The Water and Play It Again, Sam. Roberts starred in that play and also the film version. He started his acting career on Broadway. His girlfriend was starring with Robert Redford in the Neil Simon’s play Barefoot In the Park, and when Redford took a break, she suggested her boyfriend. It was a simpler time. Having auditioned four times for Don’ Drink the Water, but missing out, Allen was impressed with him in this play. According to Roberts, Allen went backstage and said[8]:

“You were great. How come you’re such a lousy auditioner?”

Roberts had also appeared in great films like Serpico (1973) and The Taking Of Pehlam One Two Three (1974).

Much like how Allen's real relationship with Keaton made it to the script, so did many aspects of Allen and Roberts friendship - including the use of their real nicknames for eachother; Max. Roberts would appear in four more of Allen's films.

Roberts' trailer was broken into during production. He lost his possessions and a script. The script was found in the garbage nearby - which Allen took as criticism. He did joke that maybe Mel Brooks stole it.

The supporting cast:

Colleen Dewhurst plays Mrs Hall, Annie's mother. Dewhurst was an experienced stage actress, and was nicknamed 'The Queen Of Off-Broadway'. Her screen roles were much fewer, and is probably best known for playing Candance Bergen’s mother in Murphy Brown. Said Allen[4]:

“I picked her not only because she’s a fine actress, but she also looks like Diane's mother. Diane's mother has that real American pioneer look, very classic. And Colleen not only had the look, but she's such a wonderful actress.”

Shelley Duvall plays Pam. She became famous for her work with Robert Altman and later appeared in Stanley Kubrick’s The Shining (1980). Like many of the roles, her screentime was reduced when the film became more about Alvy and Annie.

Carol Kane plays Allison Portchnik. She was coming off an Academy Award nomination for her work on Hester Street (1975), as well as appearing in films like Carnal Knowledge (1971) and Dog Day Afternoon (1975). She would have a long career in both film and television.

Janet Margolin plays Robin. Margolin had appeared in Allen's first film Take The Money And Run (1969). She had a career in TV since then and she would have one more significant film role in Ghostbusters II (1989). Her part was cut down as well. This was the last time she would work with Allen.

Paul Simon plays Tony Lacey. Simon is, of course, from Simon & Garfunkel, and at this point several years into a solo career to much acclaim - his last record Still Crazy After All These Years had won the Grammy for Album Of the Year. Simon would try his hand with film and after this wrote and directed a film of his own called One Trick Pony (1980). The film flopped and Simon soon returned to music, and to the top of the charts with Graceland.

This was Simon’s first foray into film. There is an irony in casting Simon in the role of LA record producer, as he is as tied to New York as Allen[4].

“I was looking for a fresh look. Somebody interesting that you don’t see acting very often. I think even that it might have been Marshall Brickman who suggested Paul Simon for the part. And it seemed a very good idea.”

Shelley Duvall and Paul Simon began a romantic relationship after meeting on the set of Annie Hall.

Christopher Walken plays Duane Hall, Annie's brother. This was one of Walken's first roles, and a breakout for him. He would follow it up with The Deer Hunter (1978), Pennies From Heaven (1981) and another 40 odd years of incredible performances. On his casting and its legacy[9]:

“That's probably why I started getting all those strange characters - because that was one of the first things I did that was seen by a lot of people. And here I was playing a suicide case ... I guess one job leads to another. The next movie I'd did was The Deer Hunter, and I shoot myself, so it's hard to get cheery parts after that.”

He was miscredited as ‘Wlaken’ in the final film. Walken had the typical brief, silent audition. His part was cut down, but it was almost cut completely.

Walken would later be cast by Allen in September (1987), but was ultimately recast completely. He would also appear, so to speak, with Allen in Antz (1998).

Not given top billing, but there are many significant cameos, including Truman Capote, Jeff Goldblum, Marshall McLuhan and Sigourney Weaver.