Jessica Rabbit, already mentioned multiple times because she’s the correct answer (and likes guys who make her laugh). And Rita Hayworth.
Seriously? Nobody’s put dibs on Bette Page?
Bette and Rose from “Rose is Rose,” particularly in her biker fantasies.
Ichabod Crane and Lincoln.
Pssst. Post #3. 
Red Monika - Cartoon, Battle Chasers comic
Dorothy Dandridge - Deceased Hottie
Pam Anderson - (Unless she counts as another cartoon, then it’s Monica Bellucci)
Cartoon: Holli Would from Cool World
Dead: Anna Nicole Smith
Slappy Squirrel and Dame Edna. What could possibly go wrong??
Dame Edna isn’t dead.
:smack:
Snoopy and Cary Grant.
Heath Ledger and Renji Abarai from Bleach. Though I like him better with his hair down.
The dead person part is so hard to choose. (Is that disturbing?). I mean, just among the classic actresses, you have Lana Turner, Rita Hayworth, Jean Simmons, Susan Hayward, Jennifer Jones, etc. etc. etc. Can’t I ask for an exemption and beg to be the meat in a Greer Garson/Paulette Goddard sandwich? Ok, if you must Daphne from Scooby Doo and Miss Goddard. Although Miss Garson, you’re more than welcome to join in;).
Me and you and a dog named Boo
Jessica Rabbit and Grace Kelly
Veronica from the Archie comics, and Veronica Lake.
That way, if I blurted out “Oh, Veronica!” in the middle of sex, neither one of them would get mad.
Gambitand either Bette Paige or Heath Ledger
Hedy Lamarr
Belle from Disney’s “Beauty and the Beast”; and Marilyn Monroe
Cartoon: the other girl from Cool World that Brad Pitt ends up with
OR
Luanne Platter
Dead woman: Bettie Page. No OR.
Comic characters are considered cartoons for the sake of this exercise, yes?
In that case, I’d say Gilgamesh Wulfenbach and Bettie Page. If I must go with someone animated, then Jessica Rabbit and Marlon Brando, circa 1951.
In either case, there should be leather involved.
How about the Bettie Page character from THE ROCKETEER graphic novel and Bettie Page? 