Yes to Gregory Peck <sigh>. He was an author in Old Gringo, but I was thinking of Beloved Infidel in which he played F. Scott Fitzgerald. Your turn.
Nightclub singer
Former First Lady
NY model
Bordinghouse owner
Literary agent
Lauren Bacall
Nightclub singer - To Have and Have Not
Former First Lady - My Fellow Americans
N.Y model - How to Marry a Millionaire
Boardinghouse owner - The Shootist
Literary Agent - Misery
Good girl! I was stuck thinking it was
Shirley MacLaine
Sorry for the delay. Yes to Lauren Bacall. (I almost put it a warning that this was not Shirley MacLaine!)
A ghost
City contractor
Entertainer (WWII)
Sailor
Author (twice that I recall)
James Caan
A ghost - Kiss Me Goodbye
City contractor - The yards
Entertainer (WWII) - For the Boys
Sailor - Cinderella Liberty
Author - Misery and Chapter Two
Alcoholic actress
Hooker
Senator
Governor
Single mom (at least twice)
for the record, mine was indeed Morgan Freeman, the fantastic actor that he is.
Yes, I think he's great. I might have to go see Dreamcatcher just to see him play a bad guy.
Marsha Mason
Alcoholic actress - Only When I Laugh
Hooker - Cinderella Liberty
Senator - I Love Trouble
Governor - Nick of Time
Single Mom - Goodbye Girl and Max Dugan Returns
Pro football player
Marine Biologist
San Quentin inmate
Detective Lieut. NYPD
Basketball coach
Nick Nolte
Pro football player - North Dallas Forty
Marine Biologist - Cannery Row
San Quentin inmate - Weeds
Detective Lieut. NYPD - 48 Hours
Basketball coach - Blue Chips
That one was Tough!
Ah, but I can see it wasn't tough enough for you Dafdaf.

Nick Nolte's the man. Your turn.
Kind of you to say so, but I very nearly gave up.
okay,
A child of diminished capacity
Stow-a-way
Criminal
Traveller
Swordsman
Leonardo DiCaprio
A child of diminished capacity - What's Eating Gilbert Grape?
Stow-a-way - Catch Me If You Can?
Criminal - Gangs of New York
Traveller - Titanic
Swordsman - The Man in the Iron Mask
Absolutely right on Leo. A magnificant actor who got bad press after a few blockbuster films that showed more glamour than genius. I recommend any who think differently to see 'Whats Eating Gilbert Grape' and be brought to tears my the young guy's performance.
The traveller role was intended to be The Beach (best i could think of without giving it away); and the criminal role was meant to be 'Catch Me If You Can' but that one wasn't such a great description - should have said 'freudster'. It did lead me to watch the film just now though, and I thoroughly recommend that one too!
Tomorrow my laptop's being repaired for a few days so I prob won't be on too much. Your turn though Mac, and keep em coming.