Jay Leno Claims He Tipped Off Hugh Grant About ‘What the Hell Were You Thinking?’ Question

When David Letterman jumped to CBS after losing The Tonight Show, he was a ratings smash, regularly trouncing Jay Leno, the man who’d beaten him out for his dream job. But Leno eventually surpassed Letterman in the ratings game, thanks to some Hugh Grant hanky-panky.

Grant was riding high from his hit movie, Four Weddings and a Funeral, when he decided to satisfy a 1995 late-night craving with a sex worker named Devine Brown. His subsequent arrest for lewd conduct, in a day when tabloids could ruin a reputation, threatened to tank Grant’s career. Instead, his fame was turbo-charged, thanks to an interview with Leno.

Leno began the interview with the question that all movie fans had on their minds: “What the hell were you thinking?” (Leno’s drummer chimed in with a rimshot.) Grant’s charming mea culpa endeared him to the public, a textbook case of how to own an embarrassing situation and move on. “I think you know in life when you do a good thing or a bad thing,” he told the spellbound studio audience. “I did a bad thing, and there you have it.”

Grant had already been booked for his appearance on The Tonight Show to promote his new comedy, Nine Months, which was opening that weekend. However, producers weren't sure whether Grant would show up, given the scandalous spotlight. 

When Grant arrived as scheduled, Leno had no choice but to catch him before the show and address the elephant in the room. “I just went in to see him, and I said, ‘I gotta ask this. I’m not going to ambush you or anything. But I gotta ask,” Leno recently told LateNighter’s Bill Carter.

Grant understood the assignment. “He was a good guy about it,” Leno claimed.

Honesty seems like the obvious play, but not every guest played ball. Leno told Carter about an Olympic athlete who’d recently posed for Playboy, but refused to answer questions about the spread on The Tonight Show. Leno couldn’t believe it. “I told them, ‘I can get a comic here in about 10 minutes. This is why you’re here!’”

Leno said The Tonight Show had been slowly gaining on Letterman in the ratings for months prior to Grant’s interview. NBC’s primetime lineup was just entering its “Must See TV” era, and CBS lost NFL football, changing the fortunes of both networks. But Leno believes that the Hugh Grant interview was the tipping point for overtaking his rival. 

Sure enough, Ad Age reported that Grant’s stammering appearance was the first Leno Tonight Show to beat Late Show with David Letterman in the ratings. It was a lead Leno wouldn’t relinquish until some of Letterman’s final farewell shows.