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Jay Leno, and different kinds of "cool"
The first time I talked to Jay Leno, he was explaining to me why he was being so mean to someone.
That’s right. Jay Leno–always amiable, always upbeat, too nice to a fault according to some critics—wanted me to understand why he didn’t feel bad about making some pretty nasty monologue jokes about a public figure.
It was the summer of 1998. I had written a column for the Sun-Times criticizing Leno for an apparent double standard. Leno had apologized for making fun of overweight bikers at a Harley-Davidson event in Milwaukee, but he wasn’t backing down from making jokes about the physical appearance of Linda Tripp, a key figure in the Bill Clinton/Monica Lewinsky scandal. (While acting as a mentor of sorts to Lewinsky, Tripp had secretly tape-recorded phone conversations in which she encouraged Lewinsky to spill the details of her relationship with the president.)
“Linda Tripp testified last week,” was the set-up for one of Leno’s monologue jokes. “For a minute, I thought they were re-running the movie ‘Tootsie.’ ”
And: “Linda Tripp has her own web site on the Internet. There’s one Web site you pray they don’t have nude pictures.”
After I wrote a column pointing out the hypocrisy, Leno called the Sun-Times city desk.
He finally reached me at home, saying, “Richard Richard Richard. Must have been a slow news day, huh?”
Leno said he was going to continue to go after Tripp.
“Linda Tripp is the lowest of the low,” he told me. “She essentially ruined Monica’s life…anything you can do to hit Linda Tripp is all right. She betrayed a friend. I’m not going after her because she’s stout, I’m going after her because she’s the lowest of the low. I don’t like rats, and I think people in Chicago understand what I’m saying.”
We chatted for a while about a few other things. Leno told me, “I probably spend an hour a day on the phone with people who have called or written with gripes.”
That was the hallmark of Jay Leno’s nearly unbroken (ahem) 22-year run as host of the “Tonight Show.” He was a people pleaser, and if critics and hipsters didn’t like it, he didn’t care. Except he did. But it didn’t stop him from going straight for the middle ground and racking up the ratings night after night, year after year.
A few years later, thanks to my television partnership with Roger Ebert, I was a guest on “The Tonight Show” two or three times a year. Siskel & Ebert had been All-Star guests on the “Tonight Show” going back to the Johnny Carson days, and Jay was gracious enough to treat me just like Roger treated me—as an equal partner in the show.
(In classic Roger fashion, he insisted I take the seat next to Jay every other appearance, just as he had done with Gene.)
I also did the show on my own a few times. I even helped Jay judge a student film contest.
Whether it was with Roger or solo, every time I was booked, the producers would ask for an early arrival—because Jay would want to come by and talk movies for a half hour or so. Sometimes the opening theme would be playing, and Leno would squeeze out one more insight about a film before they’d grab him and tell him it was TIME.
The behind-the-scenes Jay was often more critical of certain movies and performances than the on-camera Jay. “I can’t say this stuff on the show if I want [A-list actress] to ever come on again,” he’d explain.
But he knows movies. As one of his producers once said to me, “Jay cares about only a few things in life: his wife, jokes, cars and movies.”
When Roger was recovering from surgery in 2006 and needed to take some time off from “Ebert & Roeper,” we began casting about for celebrities and film critics to fill in.
It was a July night—almost eight years to the date when Leno had made that phone call to a Chicago columnist to defend his monologue jokes. After I guested on “The Tonight Show,” we waited for the show to come to a close, and then Jay and I and a few other folks from “The Tonight Show” and “Ebert & Roeper” walked across the parking lot to a studio where a makeshift version of the “E&R” set had been built. (It was the first and only time I didn’t do the show in Chicago.)
As we entered the set, Leno said, “Now I’m a guest on your guys’ show. Just tell me what you need me to do and we’ll make this happen.”
His only “fee” was a pizza delivery.
We settled into our chairs and knocked out the show in quick fashion. Then we did a few promos and took a few photos, and Leno thanked everyone and was on his way.
There was no upside to Jay Leno doing the show. He could have politely said no or begged off due to his schedule, and nobody would have thought a thing about it.
It was an extraordinarily gracious thing to do.
We’ve seen hundreds upon hundreds of stories about Leno’s legacy in the last few weeks, as he prepared to (once and for all) abdicate the “Tonight Show” throne. Sometimes I get grief on Social Media for evening mentioning Leno’s name, because of course the last time Jay Leno was “cool” was about 30 years ago, when he was the best stand-up comic in the world and he was killing it as a guest on “Late Night With David Letterman” on NBC.
But I’ll tell you. He was always pretty cool to me, whether he was giving me s— about a column, talking movies in the green room or stepping up when a friend had taken ill.