We don’t get a lot of touring standups here, so I mostly see local ones (Riaad Moosa is a particular favourite). Of course most people outside SA will be aware of Trevor Noah, seen him a couple of times.
I have seen Jimmy Carr here. Very good.
Sam Kinison was actually a Pentecostal preacher before he became a comedian, so maybe your date sensed a kinship there…?
Very funny guy; but he has one of the weirdest laughs I’ve ever heard. He sounds like an asthmatic braying donkey when he laughs 
Oh man, I’d forgotten that I’d seen him (must have been about the same time too). There was a lot of humor to his act but it was more ballet than comedy.
More recently we saw Caitlin Cook who has a show centered around bathroom stall graffiti. It’s a bit of a one-joke show but she gets a solid and very funny hour out of it.
I’m not really into standup comedy, but I do recall two acts that I saw back in the day that were pretty good.
Mark Russell, political satirist and parody artist. Entertaining guy. It was also one of my first dates with my first girlfriend.
Steven Wright, known for his deadpan delivery and weirdness. He even reacted to hecklers in that strange monotone. It was fun to watch.
Given how he is in the news now I’m surprised I forgot to mention Carrot Top. I went to the show mostly as a Vegas experience thing. I was pleasantly surprised. It was a funny show. The percentage of prop jokes was actually pretty low. He had long stretches in the act that were just standard standup and he was good.
I also saw Tom Rhodes and Dennis Regan at the now blown up Tropicana in Vegas.
In Atlantic City at the Borgota they used to have comedy shows you could get comped tickets to. It was hit or miss and I saw a bunch of comics I don’t remember but I did see Alan Havey (Mad Men) and Gary Valentine (King of Queens and Kevin James IRL brother).
For those who missed it, he survived a suicide attempt. He’s an interesting guy - at one point he got really into bodybuilding and got really huge and muscular.
I love stand up, but I can’t list a lot of famous people I’ve seen live. I did catch George Carlin while in college; his material wasn’t the best, but it was just an honor being in the presence of greatness.
I’m sorry I never got to see Ralphie May before he died; he was hilarious. Jim Jefferies is currently who I’d most like to see perform.
I love his gun control bit– it’s not just funny, it makes a lot of damn sense. It should be shown in American High School Social Studies classes or something.
Oof. Another one I’ve seen and forgotten. I recall it not being his best material, and of course political satire has a very short shelf life indeed.
I have memories (possibly false) of seeing Bill Cosby in Saskatoon in the early '80s, when I was a little kid.
But the comedy team I most remember is seeing MacLean & MacLean in Kitchener, Ontario. They were (RIP) 2 brothers who were famous for their dirty songs like “Dolly Parton’s Tits” and “I’ve Seen Pubic Hair”. My friend was dying to see them. Pretty good, if you’re into that stuff.
Standup comedian Ron White, at a casino in Hammond, Indiana, about 15 years ago; I won tickets to see him from a local radio station. About 75% of his material was new, though he did do a few of the bits which got played to death in his TV specials (e.g., “Tater Salad”), but which fans undoubtedly expected to hear. He was very funny, though I think he drank half of a bottle of whiskey over the course of his show.
Classical music parodist Peter Schickele (a.k.a. PDQ Bach), and comedy juggling troupe The Flying Karamazov Brothers, both when I was in college at UW-Madison in the 1980s.
I saw The Smothers Brothers perform their double-act in the summer of 2000. Both were in their 60s but still on top of their game, with a mix of crowd-pleasing retro material and some newer, racier bits (including the inevitable “Dick” joke.)
Like @XOldiesJock, I the first standup I ever saw was Steve Landesberg, also at a college (Fairfield) in around 1983.
In the early 90s, I was a producer on a local talk show, so we’d get a lot of acts that were doing shows at the local club, so I met Gilbert Gottfried (who borrowed a shirt from me to be presentable on air, and was a really odd guy), and Ellen, among notable names, but never really went to the club to see the acts themselves. There was a guy who billed himself as “Klaus Myers” and did his act in a German accent but was actually an a American - at one point at the club he pulled me aside and asked if my GF (now wife) knew the bit.
Years later, with kids grown and more time, we saw Gabriel Iglesias in a big arena show with our kids, and my folks - it was good family fun.
We have an outlet of The Improv near home, and there I saw Patton Oswalt, working out some new material for a special (a long, extended bit about a “barn full of clown pubes” which was uproarious) and recently, Tom Papa, who we also saw out in Palm Desert, and the great Lewis Black on what I think was his final tour.
He is excellent. He doesn’t recycle bits so he will be different every time you see him. I saw him at the Beacon Theater which is about 3,000 seats. Personally I think that comedy is superior in clubs but he was still great in a bigger venue.
Yes, that band =)
They did an absolutely rocking concert. Cheech and Chong did some classic stuff, and discussed things [one of them married the blond airhead princess’ actress from Corsican Brothers]
Just remembered something else. Bob Levy was in a car accident and couldn’t work. I went to the benefit show the put on for him. Colin Quinn, Jim Norton, Artie Lange, Jim Florentine, Vinnie Brand and Rich Vos all performed.
I just remembered a few others. The local university hosted a comedy night and their public radio station gave away tickets. There were four comics in the lineup, and I remember three of them: Ellen DeGeneres, Paula Poundstone, and Robert Klein. I don’t remember who opened for them, but these three appeared in that order. I would estimate half of their acts were what we’d seen on TV, with the rest new material. Klein did a masterful job of checking his watch, then wrapping up his act. He kind of spun around as part of a gag and took a quick peek at his wrist then called it a night. He also could not stop his leg.
I forgot Peter Schickele (P.D.Q. Bach). I’ve seen him in concert twice.
I saw Hodgman about 10 years ago when he recited his newly written narration for Benjamin Britten’s “Young Person’s Guide to the Orchestra” with the Boston Pops. (“The instruments of the orchestra can be divided into four families - much like organized crime, or the characters on Game of Thrones…)
Wow! I guess I’ve led a sheltered life. I’ve never seen a comedian live.
Does Victor Borge count?