Oddly, this kinda-sorta happened. In the 70’s, Lenord Nimoy had a one-man show, in which he played Sherlock Holmes. He even used the line “Logical.” Mom & Dad went to see it, when he played Chicago.
Diomedes~~Gargamel wants to eat the Smurfs. I don’ think this would go over too well.
Gargamel & Hannibal Lecter, though…
For some reason, I just thought of Beverly Crusher: Medicine Woman.
Bret Maverick and Jim Rockford
Dante Sparda and Vash the Stampede.
They dress similarly, tote huge mismatched handguns (well, until July at least) and bizarre inhuman Arms, like a drink or several, and have hallucinations about women who look like their mothers.
They’d probably get along famously at first, but Vash’s pacifism might start to grate after a while (especially given how good a demon hunter his skills would make him) and Vash would likely object to the bloody severed heads Dante keeps on his office walls.
Better still: Don Juan from Journey to Ixtlan and the other Don Juan – from Don Giovanni, or Byron’s long poem.
“Drugs!”
“Sex!”
“Drugs!”
“Sex!”
Maybe eventually they’d find a compromise . . .
Sephiroth from Final Fantasy and Elric of Melniboné. Both are white haired, emotionally screwed up, ultra powerful guys with big swords who bring annihilation to everything around them. Separated at birth ?
Captain Jean-Luc Picard and Gurney Halleck.
“Billy, Dolly, Jeffy, P.J. . . . Meet Freddy, Jason, Michael and Chucky!” 
We must get around to discussing why the hate for Tarl Cabot some time, given your penchant for imagining him running into archmagesses, goddesses, and now superheroines, in the name of payback. Kinda validates the Gorean angle that in the real universe governed by the familiar laws of biology and physics, males as a sex have vastly superior physical prowess.
It’s entirely possible that TC would respect the She-Hulk’s genuine ability to front up and exercise her non-gender-traditional role. Mostly, he only despises weak, competitive pseudomen who demand special privileges in order to accommodate their delusions of gender identity.
“Accidentally” maiming someone who’s annoyed her doesn’t seem to be the easy-going She-Hulk’s regular M.O. either.
Cabot makes a habit of assaulting and enslaving women where exactly? You had some cases in mind? You may find that a heckuvalot less of it goes on than you think - compared to his regular programme of saving Gor and sometimes Earth too, an average of once per book, and not unoften risking his own life for people who don’t deserve it.
The Doctor from Voyager and Dr. Gregory House. I’d love to see The Doctor’s program self-destruct.
Eeyore, Marvin (HHGTtG) and Puddleglum. Anyone not bent on becoming suicidally depresse would do well to give these three a wide berth.
I spent a good part of last season’s 24 run yelling at Jack Bauer, “Go see Mr. Universe, dammit!”
Jack Bauer and Vic Mackey. 