Nick Charles- John Cusack. With this cast, you can either have a remake that takes place now, or in the thirties when it was written. Cusack has played period well and his chemistry with Minnie Driver in "Grosse Point Blank" felt like an update of Nick and Nora Charles. He has the chops to play the sophisticated, worldly ex-private detective who married well (in more ways than one).
Which leaves his wife...
Nora Charles- Maggie Gyllenhaal. I know that Nora is supposed to be younger than Nick and Gyllenhaal is 11 years younger. But more importantly, a "Gyllenhaal Nora" would be as much of a match for Nick, as Gyllenhaal (who is one of the most interesting actresses of her generation) would be for Cusack. But what about the case itself? Clyde Wynant/Mimi Wynant Jorgenson- Philip Baker Hall/Susan Sarandon. If you'll recall Wynant is the actual "Thin Man" of the story- a brilliant inventor has gone missing and his daughter Dorothy has asked Nick Charles to help find him. Wynant is basically rude to almost everyone in his life (except for Dorothy), so it's no wonder when he disappears and is suspected of murdering his wife. Hall has played this kind of part so often he should have "irascible" stamped on his forehead. The ex-wife is the sort of flighty, high society matron that was a staple of thirties screwball comedies. In this film, she has a swarthy, foreign gigolo for husband (with the improbable name of "Jorgenson"). I think Sarandon would nail this.
Macauley- Paul Giamatti. Macauley is Wynant's lawyer and while Wynant is gone, initially, Macauley is handling all of his affairs, directed by notes sent from Wynant. The lawyer is a meek yes-man for Wynant's cruel remarks, who later turns out to be a stronger than anybody guessed. Giamatti may be a little too on the nose for this part (he's played a gazillion* variations on this type), but for supporting cast you want pros who can nail things in as few lines and scenes as possible. Giamatti is one of those pros. And speaking of pros in the supporting cast...
Dorothy Wynant- Ginnifer Goodwin. Dorothy is Clyde's daughter. She gets Nick involved in the case and is never seriously considered as a suspect. Played by Goodwin, who is making a big name for herself on HBO's "Big Love", after years of supporting work, the sweetness of the character will be sincere without cloying.
Lt. Guild- Jeremy Piven. Guild is a good dimwitted flatfoot type. Piven, who usually plays sharper guys would be great in this slight departure from his displayed range. Plus, he's in every Cusack movie. Every single one.
Chris Jorgenson- Kevin Alejandro. In the original film, this part of the gigolo was played by Cesar Romero, who was looks like he was cast because he didn't look anything like a Swedish gigolo named Jorgenson. Alejandro has been fine in television shows like "Ugly Betty" and last year's Fox sacrificial lamb** "Drive".
Albert Nunheim- Steve Buscemi. The weasel in the story. 'Nuff said.
Mimi- Amy Ryan. The weasel's girl. She has a one big, emotional scene in the film, her only scene as I recall, and you want someone who can knock it out. Ryan just got nominated (for an Oscartm!) for her small part in "Gone Baby Gone" and do the job here as well.
Tommy Quinn- Christopher Gorham.The nice guy fiance to nice girl Dorothy Wynant. Not a suspect. Gorham's been doing a great job on "Ugly Betty" as Betty's nice guy boyfriend. Do the math.
Mrs. Amelia Jorgensen- Ana Ortiz. Speaking of "Ugly Betty", Ana Ortiz could do with a big movie part and this, Chris Jorgenson's wife, would do nicely.
Julia Wolf- Cady Huffman. Wynant's floozy secretary. Seeing Huffman on "Curb Your Enthusiasm" a couple of years ago, as herself, reminded me of how good she is. She was the original "Ula" in the Broadway company of "The Producers". She'd be fine in this.
Director- Stephen Frears.This is a large ensemble, period piece who needs a director who doesn't leave thumbprints on the material. Frears is a classic journeyman director, almost in the style of W.S. "Woody" Van Dyke the director of the original "The Thin Man", and has worked with Cusack a couple of times. For this, he'd be perfect, adapting his direction, as he usually does, ot the needs of the story.
Got any better ideas?
*"gazillion" is a real number used by real number people.
**a good show that, despite critical acclaim and a small, passionate fanbase is cancelled by Fox far too quickly for it to find an audience. See "Firefly" and "Arrested Development".