LOS ANGELES — Norm Macdonald has just unwrapped his first Klondike bar when he mentions the Chris Rock show. Turns out he has a chance to appear at a surprise gig at the nearby Comedy Store that also includes Louis C.K. and Dave Chappelle.

Wouldn’t performing in L.A. with the hottest comedians on Earth two nights before Rock’s much-anticipated #OscarsSoWhite hosting spot be good for his career?

Macdonald, 56, shakes his head. His mouth is full of chocolate crust and ice cream, and he chews as he talks. He’s in his favorite chair, sneakers kicked off, ESPN on with the sound down.

“The only thing that would happen is I would destroy. Which leads to nothing.”

It is a strange mix of confidence and fatalism.

“I’m telling you, I know. As a matter of fact, if there was somebody writing a story about that night, I would not be mentioned.”

On food and medical advice
12/4/2015, 5:46 AM
Norm MacdonaldOk, I'm sure everything will be fine. Just fine. On the way back, though. Definitely on the way back. You fly so often, Geoff, that it is imperative. Pulmonary Embolisms are no respecter of a man's vocation, after all.
SEE FULL CONVERSATION

I’d mention you, I tell him. This seems to have no effect.

“I could do better than all of them. Which is possible. I’m not saying I’m better than them. I’m saying that on any night, I could do material that’s super strong and I’d probably be better than Rock’s material for the Oscars. But it leads to nothing.”

Over the next four hours, Macdonald barely budges from his seat in the two-bedroom condo he recently bought in a planned community not far from the airport. But he does talk — about his first book, a kind of memoir that is overdue and torturing him, his various TV ideas, his various TV failures, his dashed dream of hosting a late-night talk show, Rodney Dangerfield, gambling, religion, Russian literature, his son, why he was “Saturday Night Live’s” best “Weekend Update” anchor ever, why he’s a terrible actor, his obsessive tweeting and his belief that nothing is more important professionally than being the greatest stand-up comic of his time. Five more times, he will get up to grab another Klondike. And then, around 2:37 a.m., he’ll stand up, lift up his shirt to rub his stomach and say, “Maybe I shouldn’t have had all six of those.”

Stand-up comedian, writer and producer Norm Macdonald, shown in Los Angeles, could very well prefer reading “War and Peace” upside down. (Kyle Monk/The Washington Post)

If it isn’t obvious yet, Macdonald’s publicist isn’t here. He doesn’t have one. And that makes sense. This article isn’t being done because he has an entertainment product to plug, though, in the months after the Oscars, Macdonald will finish his book. “Based on a True Story: A Memoir” comes out in September.

This profile is actually a journalistic intervention. It is about trying to understand why a brilliant, original voice remains virtually invisible at a time when, as his admirer Conan O’Brien puts it, “every United States citizen who is registered to vote has a talk show.”

Comedy Central President Kent Alterman describes Macdonald’s absence from the airwaves as “one of the great injustices in the world.”

“How,” he asks, “is Norm Macdonald not on the air?”

‘If something is true, it is not sentimental’

Let’s start with the last big thing. It was about 15 months ago, on the 15th of May, 2015. Macdonald, wearing a suit and a crisp red tie, arrived at the “The Late Show With David Letterman” to perform the final stand-up set on the legendary host’s program.

He brought his best material. His timing was impeccable. And when he was done, he offered these parting words.

“Mr. Letterman is not for the mawkish, and he has no truck for the sentimental,” Macdonald said, clasped hands raised to his chin to help maintain composure. “If something is true, it is not sentimental. And I say in truth, I love you.”

And then he cried.

On Letterman
11/24/2015, 6:06 PM
Norm MacdonaldBut all opinions on comedy are secondary to David Laytermsn's.
Geoff EdgersDave is a hard get. But you have my word I will push and push and push
Norm MacdonaldThat should read Letterman. Laytermsn doesn't know s***.
SEE FULL CONVERSATION

It may have struck some as odd that Macdonald was even there. Other guests during Letterman’s star-studded final week included Tom Hanks, Bill Murray and Bob Dylan. For Letterman, Macdonald fit in perfectly.

“If we could have, we would have had Norm on every damn week,” Letterman says. “He is funny in a way that some people inhale and exhale. With others, you can tell the comedy, the humor is considered. With Norm, he exudes it. It’s sort of a furnace in him because he’s so effortless. The combination of the delivery and his appearance and his intelligence. There may be people as funny as Norm, but I don’t know anybody who is funnier.”

The problem has never been being funny, whether doing stand-up, a video podcast or another legendary talk show guest spot.

The struggle for Macdonald has always been finding the right outlet for his humor.

“Part of what makes him so compelling and so fun to watch is that he defies categorization,” O’Brien says. “He doesn’t fit into any piece of the puzzle, and I think that might have something to do with why no one has said he’s perfect to host a show.”

Like Dylan, one of his musical heroes, Macdonald is hard to pigeonhole. Just scroll through three of his must-YouTube moments.

In 1998, on O’Brien’s late-night show, Macdonald moved over a seat to make room for “Melrose Place” actress Courtney Thorne-Smith. Then he took over her segment. She was trying to promote her new movie, “Chairman of the Board,” with Carrot Top.

“I bet board is spelled B-O-R-E-D,” Macdonald snapped at one point, leaving the host doubled over in laughter.

A decade later, Macdonald brought a twisting four-minute story about a depressed moth to O’Brien’s “Tonight Show,” masterfully peppered with pauses and almost unpronounceable Russian names.

Comedy Central recruited him for 2008’s roast of “Full House” star Bob Saget. Be more shocking, he was told by the producers of a program known for its coarse, profane put-downs. No problem. Macdonald took to the dais with a stack of index cards stuffed with corny and clean one-liners.

“There are times when Bob has something on his mind. When he wears a hat.”

“It’s that kind of comedy where it’s deconstructed and served back to you,” says Steve Higgins, a longtime SNL writer and the announcer on “The Tonight Show Starring Jimmy Fallon.” “It’s the same way that Duchamp would put up a tire nailed to a stool. It also may be the reason he’s not giant. Because maybe he’s too funny.”

Macdonald, 14, lies on his family’s couch at their farm near Avonmore, Ontario, where they spent their summers. (Courtesy of Norm Macdonald)

Things you should know

Growing up in Canada, Macdonald was “one of the best-behaved children in his class.” (His mother said that.)

He doesn’t drive.

Lori Jo Hoekstra, a researcher when he joined SNL, is his closest confidante and, to date, has co-produced virtually everything he has done in the past 20 years.

He tells everyone he was born in 1963, but he was really born in 1959.

On Russian Literature
12/11/2015 5:54 PM
Norm MacdonaldDid you ever read the story about the fellow who bought an overcoat and it changed his entire life.
Norm Macdonald?
Geoff EdgersNo. I'd like to.
Norm MacdonaldWell then I will tell you.
SEE FULL CONVERSATION

There is no Uncle Bert.

He loves Russian literature. Tolstoy is his favorite.

He has been married once. He doesn’t talk about his ex-wife, a marriage therapist in L.A., though if you press, he will groan like a child getting checked for strep throat and eventually say “she’s great” and a “fine person.”

He has a son, Dylan, 23.

His parents were teachers. Percy died in 1990 of heart disease. Ferne, 81, splits her time between Canada and Los Angeles, where she makes “Norman” delicious tomato sandwiches on toasted rye.

This summer, he fired Rick Greenstein, his stand-up agent, for booking him for a June date to go on before Adam Carolla at the Kennedy Center, who he likes but does not believe should follow him. He also canceled the gig.

He prefers texting to most other modes of communication. During the course of the reporting of this story, we will exchange more than 250 messages.

On food and medical advice
12/4/2015, 5:46 AM
Geoff EdgersIf my words are a few now… It is because I am driving a stick shift, it is pitch black and I want to survive to reach you.
Norm MacdonaldOk, I'm sure everything will be fine. Just fine. On the way back, though. Definitely on the way back. You fly so often, Geoff, that it is imperative. Pulmonary Embolisms are no respecter of a man's vocation, after all.
SEE FULL CONVERSATION

He doesn’t drink or do drugs. But he gambled away everything — twice.

He is not one for parties.

Uncompromising, unpredictable

“I hate that table,” Macdonald says, glancing at a piece of furniture in his living room.

The table belonged to the late Sam Simon, famous for co-creating “The Simpsons” and becoming very rich in the process. Simon gave the table to Hoekstra, Macdonald’s producing partner. She put it there because Macdonald had no furniture.

It will be gone within weeks, but today, it’s a reminder of one more good idea gone bad.

A few years ago, Macdonald pitched a fake reality show to FX. The network liked the idea, but wanted him to get a writing partner. So Macdonald recruited Simon, a friend. They signed a development deal and wrote a script. The network loved it and was about to order a season. Except Macdonald hated the script.

“Just a bunch of nonsense,” he says now, “and Sam was in it more than me, which I didn’t expect at all.”

So Macdonald wrote another script alone. And, in what he describes as a Hail Mary, he delivered his and a revision of the original worked on with Simon.

“And I put Sam and my name on both of them,” Macdonald says. “I lied. I said, ‘We can’t decide which is better.’ An hour later, they phoned back. They loved mine. So I told them that was mine.”

That strategy did not go over well. His friendship with Simon collapsed. So did his FX deal. His TV agent, CAA’s Michael Rosenfeld, fired him.

“I think people were floored,” says John Solberg, FX’s executive vice president of communications, of Macdonald’s approach.

“In their defense,” says Marc Gurvitz, Macdonald’s longtime manager, “part of their point was, you’re going to be a writer, you’re going to be starring and producing it. We’re going to feel more comfortable if you have a right-hand man.”

Oh, one more thing.

“I do remember reading both scripts,” Gurvitz says, “and Norm’s script was funnier.”

That’s not to say Macdonald hasn’t tried to go along. Like in 2011, when Comedy Central created “The Sports Show With Norm Macdonald.” He thought doing sports would limit his audience to men. Comedy Central said not to worry. The show died after one season.

Alterman, the Comedy Central president, calls it one of “my greatest failures and successes. With Norm, I felt like I prevailed by getting him a show, but then I let him down because I couldn’t crack the code.”

Macdonald prepares backstage at Carolines on Broadway in New York on Nov. 13, 2015. (Yana Paskova/For The Washington Post)

Macdonald performs his stand-up act at Carolines. (Yana Paskova/For The Washington Post)

There is a place where Macdonald feels at home. Watching him do stand-up, he’s a master, whether delivering a riff on the sad reality of children having to go to school or the fact that Harrison Schmitt, an astronaut who was the last man to walk on the moon, “did not become famous” while “a girl with a giant ass is super famous.”

Macdonald rarely repeats jokes. He makes his work look effortless.

On Lorne
12/31/2015, 6:40 PM
Norm MacdonaldI love Lorne but have no idea what he'll say. When I did update it was the only time he didn't have control over that part of the show. Due to Downy. I will be very interested in what Lorne says. Very smart and friendly to me but not sure he liked my exit strategy that much.
SEE FULL CONVERSATION

“Which, of course, is what a pro is supposed to do,” says Lorne Michaels, the SNL creator. “I used to say when Fred Astaire dances, he doesn’t grunt to let you know it took him six hours to learn that step. And Gordie Howe, you could never tell how fast he was skating.”

Too often, Michaels laments, Macdonald’s four-year tenure on “Saturday Night Live” is reduced to the moment, just before Christmas in 1997, when NBC executives forced him off “Weekend Update.” (Reports stated that NBC’s Don Ohlmeyer was angered by the relentless stream of jokes about the executive’s golf buddy, O.J. Simpson.)

More important is what Macdonald did when he took over “Update” in 1994. He wasn’t cutesy. He didn’t roll his eyes in self-deprecation when a joke was too mean. He called the segment the “fake news” and committed in an almost confrontational way.

“He would stare the audience down,” says Higgins. “If you like it, that’s your business. If you don’t, that’s fine, too.”

Macdonald loved the idea of stripping material to its bare essentials. He thought the ultimate “Update” joke would be where truth and fiction were one.

A favorite:

“Julia Roberts told reporters this week that her marriage to Lyle Lovett has been over for some time. The key moment, she said, came when she realized that she was Julia Roberts, and that she was married to Lyle Lovett.”

Kevin Nealon, left, and Macdonald perform a sketch during Weekend Update on “Saturday Night Live” in 1994. (Gerry Goodstein/NBC/NBCU Photo Bank via Getty Images)

Michaels does not look at Macdonald’s career and wonder, as others do, why he isn’t playing to a larger room. Instead, he looks at his steady slate of stand-up gigs and ability to stay in play with TV networks, even though he’s never been given a fair shot at hosting a late-night talk show.

Michaels then brings up Don Rickles, the famous put-down artist who, at 90, continues to perform.

“Rickles is one of the funniest people that ever lived, but he’s not for everyone,” he says. “Whenever I’ve seen Norm live in any kind of performance situation, he’s brilliant. We talk about wishing more people knew Norm and that he had more commercial success. Is he perhaps not meant for that?”

A clip from the 2012 TBS pilot “Norm Macdonald Is Trending,” which never aired on the network. (Norm Macdonald)

A clip from the 2012 TBS pilot “Norm Macdonald Is Trending,” which never aired on the network. (Norm Macdonald)

Always wanted, ‘impossible’ to get

He is not anti-social so much as socially reluctant. In an industry centered around parties and red carpets, he prefers the privacy of his home or, after a gig, clicking through the channels in his hotel room.

“I’ve been to six Hollywood parties and out of those six, I probably got two jobs,” Macdonald says. “In other words, if I went to 600, I’d probably get 200. Somebody at the party, when they’re auditioning people the next week, they’ll go, ‘Hey, Norm was funny at that party at Kimmel’s house.’ But if you’re not around, it’s not their fault. They forget you’re alive.”

On planning
11/30/2015, 4:51 PM
Norm MacdonaldWhat do you want to do?
Norm MacdonaldDo you have a car. I don't have a car. I don't know how to drive.
SEE FULL CONVERSATION

His friends try to get him out.

“Anytime I go to L.A.,” says Colin Quinn, who replaced Macdonald on SNL’s “Update,” “I’ll call [David] Spade or [Adam] Sandler or Chris Rock and we’ll say, ‘We should go out and hang out or go to dinner.’ Someone will say, ‘Did you call Norm?’ Norm either doesn’t call you back or two days later, he’ll say, ‘Where were you?’ Or he calls back and says, ‘Where are you guys going to be? What time are you going to be there?’ Or he’ll ask 15 questions that someone who is really on his way will ask but never show up.”

“I’ll text him,” Spade says. “ ‘Hey, Norm, do you want to do a show with me at the Comedy Store?’ Two days later, ‘Norm, do you want to do a set?’ All right, I guess you’re not coming. Then, a week later, you get ‘Dave, we could do a show together.’ ‘Norm, you didn’t even answer me or acknowledge it.’ ”

It can be just as hard to get him to show up on late-night TV.

“It’s nearly impossible,” says Paula Davis, O’Brien’s longtime booker. “I ask every few months, and I pretty much know what the answer is at this point.”

He makes a living off his stand-up gigs, generally favoring St. Louis or Calgary over New York or L.A. He has a steady stream of small parts on television and movies. (Netflix recently announced Macdonald would do one of the voices in “Skylanders Academy,” an animated, children’s series premiering later this year.) But some of Macdonald’s best work comes at home, sitting at his laptop.

It’s hard to imagine a comedian better suited to Twitter. His stories, launched at any time of night and often erased within hours, range from the tale of a supposed train ride (“The porter’s good to me. I tip a lot, and HE makes sure the Wild Turkey 101 touches the rim of the glass, real glass too”) to the account of his failed attempt, for SNL’s 40th-anniversary special, to get Eddie Murphy to play Bill Cosby.

There are times when Macdonald’s online activity confounds his friends.

“He’s on Twitter and he’s talking about the length of putts during some PGA tournament for six hours straight,” Spade says. “I don’t even know if it’s comedy. It’s getting into that Andy Kaufman area.”

Based on a true story

“I feel like, near the end, it just turns into a cliche,” Macdonald says. “I wish they had ‘cliche check.’ ”

He’s on the phone with his book editor, Laura Van der Veer. He’s walking around his condo as he talks.

“Based on a True Story: A Memoir” is a driving, wild and hilarious ramble of a book, what might have happened had Hunter S. Thompson embedded himself in a network studio. It’s told by a Canadian-born comedian named Norm Macdonald who gets hired by Michaels to star on SNL with Adam Sandler and Chris Farley, makes movies, a couple sitcoms and then flames out. That’s all true. The rest — you’ll have to decide.

Writing a book has been hard. There were moments he grumbled to his mother that he should have hired a ghostwriter.

“I can’t imagine how anyone likes to write a f------ book,” Macdonald says to his editor. “I couldn’t hate it more.”

On book editors
12/10/2015, 7:38 PM
Geoff EdgersLaura is a nice person. We had to reschedule but sounds like you're in good hands.
Norm MacdonaldYou're not gonna win a Pulitzer with filth like that. Laura is an innocent girl and no one is " in her hands."
SEE FULL CONVERSATION

Van der Veer tells him that she thinks Spiegel & Grau will ask him to write another. His mood brightens.

“You think they’re going to? Wouldn’t they wait to see if anybody buys this book? That’s nice. I don’t know if I could do it, though. It’s just so hard.”

Talk turns to the book cover. The publisher wants an author’s photo. That’s normal.

“I would rather have no picture if it’s possible,” he says and begins to describe a concept the reminds him of “The Catcher in the Rye” cover, though “not the one with the weird art but the other one that’s just maroon and has sort of gold letters.”

The cover of “Based on a True Story: A Memoir.” (Random House)

In the end, they settle on a small picture of his head imposed on a rusty, busted neon sign.

“Based on a True Story” may not join Aziz Ansari or Tina Fey on the bestseller list. But it should. As funny and ridiculous as it is, the book is also quite moving in spots. At one point, Macdonald writes about the fleeting nature of fame.

“I think a lot of people feel sorry for you if you were on SNL and emerged from the show anything less than a superstar,” he writes in what is labeled “The Final Chapter” but, naturally, comes two chapters before the book ends. “They assume you must be bitter. But it is impossible for me to be bitter.

“I’ve been lucky. If I had to sum up my whole life, I guess those are the words I would choose, all right.”

If it sounds sentimental, just remember: It isn’t if it is true.

Norm Macdonald in Conversation with Geoff Edgers Sept. 22. (Discussion with Norm Macdonald and Washington Post reporter Geoff Edgers at 7 p.m.) Tickets: $23-50. Sixth & I, 600 I Street NW, Washington, D.C. Call 877-987-6487 or visit sixthandi.org.

Videos by Erin O'Connor | Design by Ashley Wu | Production by Caitlin Moore

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