Yes, indeed. Custer is the answer. Your turn, Hiama.
Barbra Streisand
Dustin Hofmann
Julie Andrews
Robin Williams
Jack Lemmon
Similar role
Cross dressers
Barbra Streisand - Yentl
Dustin Hofmann - Tootsie
Julie Andrews - Victor/Victoria
Robin Williams - Mrs. Doubtfire
Jack Lemmon - Some Like It Hot
Oh that was too easy-well done Macsm11
Character's profession:
George Sanders
Christopher Walken
Woody Allen
David Niven
Cary Grant
George Sanders - Dr Andre Marbel- Paris after dark
Christopher Walken - Dr Michael Anthony Brace-Brainstorm
Woody Allen - Dr Noah- Casino Royale
David Niven - Dr Anthony Stanton-The Other Love
Cary Grant-Dr Maurice loman-Kiss and Make Up
No, I wasn't thinking of doctors. They have another profession in common!
Clue please , its driving me a little mad
Theatre Critic. But, I have to come back with the movie for Cary Grant.
Yes to theatre critic.
Do you want a hint on the Cary Grant movie?
Here's what I came up with.
George Sanders - All About Eve
Christopher Walken - Illuminata
Woody Allen - The Impostors (unbilled as Theatre Critic)
David Niven - Please Don't Eat the Daisies
If the above are right, yes please, a hint for Cary Grant.
I was thinking of Play It Again, Sam for Woody Allen.
For Cary: it's a classic that you've seen more than once. He has to deal with his various family members and their unusual tendencies.
Oh my! Arsenic and Old Lace. I have to see that one again.

I never saw Play It Again Sam. I'll have to catch that one, too.
A role in common.
Kirk Douglas
Paul Newman
Errol Flynn
Jon Voight
Burt Lancaster
They've all played generals:
Kirk Douglas - Is Paris Burning? and Top Secret Affair
Paul Newman - Fat Man and Little Boy
Errol Flynn - They Died with Their Boots On
Jon Voight - Most Wanted
Burt Lancaster - The Skin, Twilight's Last Gleaming, and Seven Days in May
Ah yes, Mac, they all did play Generals, but that's not what I'm looking for. Does it help if I add Robert DeNiro? I'm not looking for a title, or a particular individual. They all earned a living doing the same thing.