Bing Crosby
Catholic Priest - Going My Way; The Bells of St. Mary’s
Time traveler - A Connecticut Yankee in King Arthur’s Court
Spike in Rugrats Go Wild was a dog, not a baby. (Specifically, Tommy’s dog Spike from the Rugrats TV series; Bruce Willis was the voice that only Eliza Thornberry could understand, as she can talk to all animals.)
Willis was Mikey in both Look Who’s Talking movies, which I am assuming is why the clue said “more than once”.
Thanks for that. I just assumed Spike was a baby, and since Bruce voiced Mikey in both movies it doesn’t matter, but it’s good to stay on top of these things.
And BING CROSBY is the right answer.
The Socialite is from High Society, the character is C K Dexter-Haven.
Con man: pick any Road picture with Bob Hope.
Bandleader: Dr. Rhythm, among others.
Drunken doctor in a western: from Stagecoach
PR Man for a gangster: Allan A Dale in *Robin and the 7 Hoods *
A soldier (at least twice)
A sailor
A vacuum cleaner salesman
A professional wrestling referee
A jockey in a horse race
Lou Costello?
Soldier in Buck Privates, Sailor in Abbott & Costello in the Navy, jockey in*** It AIn’t Hay***, vacuum salesman in Little Giant…
Correct. Professional wrestling referee in Abbott & Costello in the Foreign Legion; also a soldier (at least at the start of the film) in Buck Privates Come Home.
Demented gold miner
Symphony orchestra conducter
Treasure hunter
Architect
Theoretical physicist
Transit cop
Sportswriter
Vaudeville comedian
Document forger
President of the United States
Psychiatrist
Record company executive
NFL quarterback
President of the United States
Record company executive
Taxi driver
Even though two of the roles are the same, the answer is an entirely different actor
Walter Matthau
Gotta run; will post my own question later.
You are correct, sir!
Morgan Freeman?
Jamie Foxx? President in whichever White House attack movie he was in, taxi driver in Collateral … and the other two. 
absolutely right- he was Einstein in IQ, a transit cop in **The Taking of Pelham 1-2-3, ** sportswriter Oscar Madison in The Odd Couple, and a vaudevillian in The Sunshine Boys
No- I’ll give a hint: He’s English
Bingo- taxi driver in Collateral, quarterback in Any Given Sunday, record exec (a thinly disguised Berry Gordy Jr.) in Dreamgirls, and President in the recent White House Down.
Correct.
Donald Pleasance
Document forger: The Great Escape
President of the United States: Escape From New York
Psychiatrist: Halloween
Record company executive: Not sure. Cul-de-Sac, maybe?
New one
Circus freak
Painter
Stripper
Vampire
And still waiting on this one (so I’ll add a few more)
Presidential assassin, failed
Presidential assassin, successful
Vampire
Wizard
Spy
Drug dealer
Cop
Punk
Salma Hayek? I don’t know about the circus freak one, but the others are the Kaho biopic that I believe was just called Frida, Dogma, and From Dusk Till Dawn, which I’m pretty sure she was in but I never actually saw.
I think that’s Gary Oldman–Dracula, Sirius Black, Commissioner Gordon, and Sid Vicious all fit in that set.
And now I have to think one up.