Norm Macdonald Interview: Bob Saget Roast; 'Who Wants to Be a Millionaire'; Gambling Stories

Norm Macdonald died today. He was one of my personal favorite funny people of all-time. I was lucky enough to interview Norm in 2011, ahead of the debut of his short-lived Comedy Central show, "Sports Show With Norm Macdonald." Getting to sit down with Norm Macdonald for an hour to ask him about some of my favorite things in comedy (the Bob Saget Roast, the Frank Stallone punchline, and his underrated sitcoms) was a career highlight at the time and that hasn't changed. I've tried to add as much supplemental material as possible.

The following interview took place in New York City on March 31, 2011 and was originally published in two parts on April 2011.

Before we dive into this, let me say that Norm has been one of my favorites since his time as the Weekend Update anchor. It was kind of surreal to sit down and speak with someone whom my friends and I have watched and quoted for what seems like our entire lives. I like to think that I didn’t break into my own personal version of The Chris Farley Show, but who knows. The temptation to stop the interview at a random moment, pick up my voice recorder and say, “Note to self…” was hard to deny. I like to think I didn’t break. I think I even made Norm laugh once or twice. Basically, it was the highlight of my career as an interviewer, blogger and fan of comedy. Enjoy.

Part 1: Norm on sports blogs, gambling and Dennis Rodman

SD: I watched your stand up special. (Me Doing Stand Up) How long have you been working on that material?
Norm MacDonald: I don’t know. I’ve got a lot of stand up. It came together pretty quickly. There was only one piece that took a long time. It took me like 6 months to figure out.

SD: Which one was that?
NM: The one about murdering a woman. I mean, that took a long time. It’s a very delicate piece to get laughter from.

SD: Do you preform live a lot?
NM: Yeah, yeah. I love doing stand up. Ever since I started doing show business, I’ve done stand up and everything else was just a side thing.

SD: Do you tour much?
NM: I tour all the time. I live in LA. If I was in New York, which I – God I so wish I lived in New York. You must be so sick of hearing me say that. (This was directed at a PR person in the room. Norm had never told me he wanted to live in NY.) New York, you just [go] from club to club, its really fun to do, but LA’s not like that. So, yeah, I’m always on the road.

SD: How long have you been working on this show?
NM: We taped a presentation for it in like in, f-ck, I think it was November or something like that. And then, yeah, I think it was November. It took us, we worked out it for about a month – The presentation I guess they call it – in November. Then we just waited to hear, then we heard in February, or something like that. Since then we’ve just been trying to get together pre-taped pieces and stuff because we can’t really write the jokes for it until the week of the show.

SD: What’s the breakdown going to be of pre-taped segments versus breaking news?
NM: It’s going to be mostly that week’s jokes. We’re going to have that week’s jokes, we’re going to try to do a sustained editorial piece for one piece and a pre-taped thing for one piece. Sports jokes will be the engine throughout the entire thing. Because that’s what I like doing. I don’t like doing man on the street things. They seem to be done to death.

SD: It’s kind of like getting back to the Weekend Update stuff.
NM: Yeah, yeah, I love the Weekend Update stuff. We’re – I’m trying – there’s a lot of internal discussion, but I’m trying to make this as close to Weekend Update as possible because I really liked Weekend Update.

SD: With the immediacy of the internet, are you worried that all the good jokes are going to be taken by the time you air?
NM: Well, luckily, the good thing is that we have sports because, my God, if you have a talk show monologue. That’s a way harder scenario because there’s 400 talk shows so I don’t even know how those guys write monologues because every joke would already be done. At least with sports… I wanted to do it live, but, uh… Comedy Central wouldn’t let me do it live. So we’re going to do it the night before. We’re going to do it Monday night. Show it Tuesday. So we’ll be really close to live-to-tape, so the stuff we’ll do, it will almost all be about that weekend, Saturday and Sunday. All the jokes will be about Saturday and Sunday.

SD: What kind of writing staff do you have?
NM: We have the two guys I wrote Weekend Update with. Like, they’re the best writers. They’re like the best writers I love from the Letterman Show. The original Letterman show that are really awesome. They all know sports like crazy. Then we have 4-5 guys who don’t know nothing about sports. We feel like its important to pull us back and not get to arcane because it will all drift into like, jokes that only like five people will understand. Then on the pilot they’re like We had to cut down – I’m like, what’s wrong with that joke? – No one understood it. No one knows who that guy is. 

NM: So, we had to make it accessible. We have a lot of guys reigning us back from getting too… Cuz I can really get into the minutia of shit. You forget that the people on Comedy Central, it’s not a sports talk radio network. So we have to make it accessible to everyone.

SD: Is the pilot going to air? (The pilot was funny, but most of the subject matter was obviously from the Fall.)
NM: No, the pilot’s not going to air. Probably a piece from the pilot is going to air. I saw this guy on the Internet, the guy who did the MMA thing. That Kyle kid, I really liked him on the Internet, I laughed so hard. So I was like let’s get this guy. This guy’s fucking awesome at interviewing.

[That guy was future SNL cast member Kyle Mooney. Here's the segment.]

SD: So he wasn’t really your nephew? (This was a joke and I swear it made Norm laugh.)
NM: No he wasn’t my nephew. So we’re going to send him to like three or four events. I think we’re sending him to NBA playoffs and shit. I want to get other correspondents too. I want to do that thing on Update where you bring the guy out and he talks straight into the camera. I like the immediacy of looking right into the camera much more than edited pre-taped pieces.

SD: Doing the sports show, there haven’t been many comedy sports shows that have worked.
NM: No, they never worked.

SD: Do you guys read a lot of sports blogs?
NM: Yeah, they do more. I read sports blog somewhat, but I’m kind of addicted to listening to sports radio. I have been for a long time. I get it mostly off FM. And also, I’m just learning computers. For the last f-cking week, people have been trying to explain blogs to me. I didn’t even know what they mean because we have our own internal blog. They keep telling me and I still don’t understand. Finally when I understand I’ll understand. But again, like you don’t want to get too arcane. I’m now watching a lot of sports blogs on the computer.

SD: How are you liking Twitter so far? (@NormMacDonald)
NM: Oh, Twitter. I didn’t know how to do it a month ago. Now I’m f-cking addicted to it. I love it so much. I didn’t understand what it was. I never understood it. I was like why the f-ck would some guy… who the f-ck cares if Sean Penn is eating a hamburger? You know? I never understood why anybody was on it and then a guy taught me to do it and I can’t stop. I’m like everybody else. I was thinking of starting separate Twitters. I’m thinking of doing a sports twitter since the Sports Show is coming up. I think I’ll do that.

SD: I saw your video that you posted with your bracket.
NM: Yeah. F-cked up that, man. I love that I put that on video. Two out of 5.9 million they said had the Final Four on ESPN. Don’t know what happened to those two.

[This was the year where Kentucky, UConn, Butler and VCU made the Final Four.]

SD: Yeah. I doubt they know much. It’s like buying a lottery ticket.
NM: Yeah, that’s about the only way you could do it. One guy said his kid picked. If you were knowledgeable, it’d be impossible to pick that.

SD: With more personal life stuff of athletes coming out, does any of that factor into your gambling picks?
NM: There’s a guy I know that does a blog. I know this kid because I used to gamble and shit and I knew handicappers and stuff. And this guy, he used to play poker with me. Nate the Great. But he does a New York Times blog where all he does is crunches numbers and the odds, he tells the exact percentage that that team will win. He crunches numbers and he sims the thing a million times and wait, what did you ask me? I feel like I’m on Adderall.

(Norm was mainlining coffee that day. He asked to be cut off multiple times.)

SD: Stories about players personal lives factoring into gambling picks? 
NM: No because that’s what this guy does. He puts ah… I’ll tell you one thing I did one time. When I was really into my gambling. I was at Saturday Night Live and Dennis Rodman came into the show. He was a guest on the show and the Bulls were playing the next day against the Knicks at noon, right? I said, Dennis Rodman is f-ckin' there, he’s got like 8 wh--es, he’s smoking weed and shit. All of a sudden, like, we’re at the after party, its like four in the morning, the guy’s still drinking and partying. I’ve got this inside information. He’s probably going to suck the next day. So I bet against the Bulls and he had like 300 rebounds and like what? I guess these guys can just… I guess especially with basketball you just be stoned and play the f-cking game. That was my one time I thought I had inside information.

(CONTEXT: On May 11, 1996, Dennis Rodman made an appearance on Saturday Night Live. The Bulls played the Knicks at Madison Square Garden at noon the next afternoon and Rodman grabbed 19 rebounds in 41 minutes as the Bulls took a 3-1 series lead in the Eastern Conference semifinals. That’s why he’s a Hall of Famer.)

SD: If Sports Show becomes a big hit, do you think you’ll be asked back to host the ESPYs?
NM: I’d love to host the ESPYs. When I did the ESPYs, what was interesting was, you know the athletes were here and they comprised a small amount of the audience. And behind them was the crowd, the New Yorkers you know. When I was doing it, the crowd loved me and I had no idea the athletes f-cking hated my guts. Then I see it on TV and I do a joke and the cut a scowling guy. I was like “Oh God, I like that guy and now he hates me. But all my heroes… But Tiger laughed! It was a pro-Tiger joke, but Tiger laughed. He’s my hero. I love Tiger.

SD: So there’s not much Tiger material in the new show?
NM: I’m not going after Tiger. I’m not going after anybody really. I’m such a sports fan. Like you were saying, sports shows haven’t really… I don’t think they’ve succeeded because in general they haven’t really been sports fans viewing them. I don’t give a f-ck about guys’ personal lives. I’m not going to be unfair to them. I think its ridiculous that Plaxico Burress is in jail for f-cking shooting his own leg. I think that’s crazy. I really feel sorry for him. I’m not going to make fun of people just because. I love sports and I’m not going to attack anybody. Like O.J. Simpson wasn’t an athlete at that point. That was like beyond sports. I don’t like Ben Roethlisberger but, you know, guys do things, they commit adultery, I don’t give a f-ck about it.

Part 2: With Norm on The Saget Roast, Who Wants to Be a Millionaire and Stan Hooper.

SD: Would you describe your humor as sort of “anti-humor?”
Norm MacDonald: Um, no. Some of it. A little bit. It depends. I like to f-ck around with comedy sometimes. I experiment with it. Like with stand up, I don’t do any anti-humor because its just not fair to the audience, you know, when they’re paying and stuff like that. Sometimes when I’m not being paid or something.

SD: Like the Saget Roast?
NM: Yeah, like the Saget Roast. That was just a little bit of an experiment. I can’t insult people. I don’t know how to insult people and call them names and stuff. Because I would feel really bad because everything you say, it has to be like true, you know, or it doesn’t make any sense. So I couldn’t do that. I could never do it to a great actor or somebody I didn’t really know. I couldn’t say, “Oh, Betty White, what’s wrong with your vagina?” Whatever the f-ck they say. I couldn’t even look at, I couldn’t even think of doing it. So Saget kept bugging me to do it. And then I thought of this idea on the last day. I said, alright, I’ll do it. And then that day, I was going to do it I was thinking what the f-ck am I going to do? And then I thought it would be a fun experiment to try to do – ‘Cuz comedy is like a number of things and one is the joke, it has to be funny.

NM: So I thought I would do jokes that aren’t funny. Another thing is delivery. So what if I did the delivery wrong also. All that would be left would be context. Just the idea of someone doing bad jokes. I got the idea because the guy told me, you’ve got to be shocking. The producer of the show, “Just try to be shocking!” So I thought, well, that would be the most shocking thing to do would be… I found the jokes in a book my dad gave me when I was a kid called Jokes For Retirement Parties. When I started stand up, that’s when he gave it to me. It was really sweet of him. Like he had this stupid, f-cking corny book, “Hey maybe this will help.” And its all these jokes for a guy’s retirement party. I’ll just take the jokes out of there. There are all these super old references. But that was just a little experiment. It angered a lot of people.

SD: I have to say, the clip is one my friends’ and my favorite roast segments.
NM: Oh really? Cool. Sometimes, it’s hard to do. You don’t know what you’re doing because when you’re standing up there. The entire time I was staring into the scowling face of Alan Thicke. He was like sitting at a table. And he just f-cking hated me the entire time.

SD: So you won’t be doing roasts again anytime soon?
NM: No, you can only do that once.

SD: Is the biggest regret in your career passing on the million dollar question?
NM: Yeah. (No hesitation whatsoever.)

[The final question starts around the 23-minute mark.]

SD: Really?
NM: Yeah, thanks for bringing that up. I really do – I do think about that a lot. I f-cking think about that a lot. And actually, that had to do with gambling also, strangely enough. Because there were two – there was a big mistake I made in that. Which is I thought Regis knew the answer to the f-cking questions. And it turned out later that people told me no he doesn’t know the answer. So I thought he was giving me verbal clues, like “Are you sure?” And I’d go “Yeah, it’s the Southern Cross.” And he’d go, “Are you sure? You can use your lifeline.” I’d go, “Oh, OK. I guess.” So I f-cking threw away all my lifelines with ones I knew and I get to the f-cking last one, pretty f-cking sure I know it…

NM: What happened was during the commercials we were backstage. And Regis is a huge fan of Notre Dame. So we’re watching Notre Dame play and I had like fifty thousand dollars on the game. And Regis was like “What the f-ck? What’s wrong with you?” I had money on the game and I told him how much. So then when we got back, now when I watch the f-cking clip, which I’ve seen like 200 times to relive my nightmare. When I f-cking saw it, suddenly I realized when I saw the clip, he goes, “You’ve got a bit of a gambling streak in ya don’t ya? You want to beat the game.” And was like, “Holy f-ck, he thinks I’m on…” Now when I look back on it, I thought he was saying “F-ck it! Don’t f-ckin.. It’s the wrong answer. Do no f-cking risk it.” You know what I mean? But now looking back at it, he saw some f-cking idiot fucking backstage sweating like a pig watching the Notre Dame game. He thought I was just wildly guessing at the final answer. But yeah, man. I wanted the balloons and money to fall down so f-cking much. If you don’t win it all, you’ve f-cking lost in my opinion.

SD: I’m sorry for taking you to that dark place.
NM: Yeah, man. That was cruel. And f-cking thing lives in forever on the f-cking computer. Honestly, I almost never watch myself, but I’ve watched that so many f-cking times. Just like masochistically.

(It should be noted that Norm was also laughing while telling that story. I didn’t dare ask him if Paul Newman ever had the chance to yell at him.)

SD: How do you like hosting High Stakes Poker?
NM: Oh, I love that. That’s really, really fun. You know, I’m a little bit conflicted because I really  love poker and I love Gabe Kaplan. You know, Gabe Kaplan is a way better poker player than me and a way better poker analyst than me. He’s really f-cking good. He’s my favorite poker analyst. I was kind of bummed that he left because I’d rather watch him than me, but it’s fun to do. It’s kind of hard to do because you see their hole cards and its hard to go, like, “What the f-ck’s this guy thinking? Clearly the other guy has a 6!” So I was trying to do it – I was saying, “Can we block the cards from me?” That’s how I did it. I got them to block the hole cards for me so I wouldn’t see the f-cking hole cards. All these guys, they can see the hole cards so it’s so easy to be like “What’s this guy? Why is he? It’s obviously a bluff.” If you hide the hole cards it's way harder to do. Then it's real game.

SD: Which brings me to my next question, have you ever run into OJ or Frank Stallone?
NM: I did run into OJ actually. Frank Stallone, I met his brother and he told me a funny story. He was like, “Hey, take it easy on Frank.” I said f-cking, “Yes sir!” He told me this funny story. He said when he did Rocky in Philadelphia, he said right after he did Rocky, his brother decided to become a boxer. Frank, you know. So says f-cking everybody in Philadelphia beat the shit out of him. Like, “Hey, I get to beat up Rocky’s brother!” I guess Frank was never the same after that. All these ring guys were like, yeah where’s Rocky’s brother?

NM: Yeah, I did bump into O.J. once at a golf course.

SD: Did he know who you were?
NM: It was f-cking so bizarre because I was with Kato. (As you’ll see in the Millionaire clips above, Norm and Kato were friends.) I was golfing with Kato and, uh, he was like on the next green. And Kato said, “Let’s run away.” I was like, no. Let’s go talk to him and he’s like, “No, no.” But Kato was my ride, so I had to go with him so I didn’t get to meet O.J. But I have a feeling that O.J. wouldn’t give a f-ck. I don’t think even think he’d be mad. I remember one time he was interviewed by Chris Myers after the murder -I mean after the acquittal. All the questions were about the murder, you know? Then at the end, O.J. says, “Oh, by the way, Thanks for all the football questions.” As if he’s going to ask him football questions. It was so funny.

SD: When was the last time you went out for a beer with Don Ohlmeyer?
NM: I have nothing against Ohlmeyer. He’s a good guy. He invented the Skins game. I always like Ohlmeyer because I always likes sports and he did so much big shit in sports. He just f-cking didn’t know anything about comedy. It’s not his fault. He’s just a big idiot. I mean, hey man, he invented the skins game. He’s a good guy.

SD: Which show do you wish you could bring back, if either: Norm or A Minute With Stan Hooper?
NM: If I could bring it back? I’m kind of uncomfortable acting, so I’d much rather do Weekend Update or the sports show, but between the two, I would rather bring back Stan Hooper.

SD: Why?
NM: Because I had an idea for Stan Hooper that never got realized. You know? Stan Hooper was like this experiment I was doing that never got off the ground. The idea of it was, it was supposed to be like a traditional show and then at the end of the first year, a drifter comes into town and kills my wife. And then the next thing I wanted to change was make it crazy, to lure the audience into thinking it was one show and then just f-cking do a hay-maker at the end of the season, but they never let me get that far. They knew what I was going to do. I explained it to them and they agreed with it and everything, but it never got there. It was all set up and it was becoming more subversive every show, but only did like 10 shows or something.

NM: I had it mapped out for like 25 shows, exactly what would happen. We only got to ten. They thought it was some wholesome show. The audience didn’t know what was going to happen. One of my many failed experiments.

SD: Are you still close with any of the guys from SNL cast?
NM: Looking back on it those guys were… I knew at the time they were the funniest guys in the world, but there was Sandler, Farley, Spade, Rock had left, but he was still hanging around… And I knew most of them from stand up anyway. We weren’t really sketch actors. We were just like.. Just to be in the room with them. Sandler throws me into a movie once in a while. Kevin Farley’s out here. We stay close. Sandler, Spade, Schneider, Tim Meadows. We all hang out still. It was such great fun. I was lucky to be with those guys. They were the funniest guys. Especially Chris Farley.

Unfortunately, the interview ended here. I was getting ready to ask him about Artie and honestly would have sat and listened to him talk until security dragged me out of the building. When a PR person told him I had traveled all the way from Albany, he let loose a patented, “Good lord!” To quote Chris Farley, “That was awesome.”