TV/Movie casts with the widest range in terms of how pleasant you'd expect having dinner/coffee with them would be

I was thinking picking any two cast members of Newsradio is a real high roller gamble...
I guess more recently, the cast of Succession?

community

well, i guess that's just 6 lovely people + chevy chase

i wonder if you'd include dan harmon in that mix, and which era...

Sons of Anarchy - Ron Perlman and Katie Segal but also the actual Hells Angel who was arrested for sexual assault.

A lot of shows have that one guy. Like Mr. Show with the Jan. 6 Rioter.

Cheers. Great cast, but at least two wing nuts (Woody, Kelsey) and one archconservative (Ratzenberger), at least now that Kirstie Alley is out of the equation.

The Cosby Show

re: Mr. Show, given how well Jay managed to hide his wingnuttery from the cast, my hunch would be in most casual settings, David Cross would be the insufferable one!

Arrested Development

Mr. Rogers Neigborhood

The Cosby Show

don't leave your drink alone with Bill

Twin Peaks

David Fincher's serial killer chat 'em up MINDHUNTER

Re: Mr. Show Jay was probably normal in the 90s, and became one of those people the internet and Covid broke.

curb your enthusiasm is a good one, with jb smoove, susie essman, and ted danson being great hangs, jeff garlin being terrible, larry being larry, and cheryl hines being married to robert f. kennedy jr.

I feel like curb might start out deceptively cordial but someone's appetizer order would go awry or RFK Jr would handle some community breadsticks with visible flaking scabs on his fingers or something and it would escalate to be exactly like being in the show.

Then there’s That 70s Show where maybe Topher Grace and the parents were the only non-horrible people.

The Apprentice
Triumph of the Will

Idi Amin: Dada

Justified, especially the season with Michael Rappaport.

Had no idea about Woody Harrelson. Ugh

Early 90’s SNL offered up Phil Hartman, Kevin Nelson, Jan Hooks and Tim Meadows on one side, and (ugh) Dennis Miller, Victoria Jackson, Rob Schneider and Dana Carvey on the other.

Triumph of the Will

You don't have to wonder what this would be like, Hitler kept a stenographer at all his after-dinner soirées to notate the conversations.

Just thinking of the distance between the two leads in Roseanne alone...

It's probably not what the OP imagined, but the various different strands of When Louis Met... have a pretty wide range.

I mean, you have Anne Widdecombe and the Michigan Militia, who may not be likeable but at the very least would be interesting dinner party guests, but on the other hand you have Louis Theroux himself, who strikes me as a detached figure who would spend the entire party checking his emails while answering questions with "yeah", and "ha", and "my agent suggested it" before leaving early.

I was trying to find a way to get Jimmy Savile into the answer, because he would not be a pleasant dinner party guest. But he generally wasn't part of an ensemble, because he didn't get on with others. To put it mildly.

Jim’ll Fix It vs The Apprentice