Jimmy Fallon ran out of questions for a Hollywood icon on ‘The Tonight Show’ and it got really awkward
When Jimmy Fallon hosted his very first episode of ‘The Tonight Show’ back in March 2009, he was quite eager to impress. Wanting a big name to kick the show off well, Fallon reached out to Robert De Niro, hoping the star power of such an iconic actor would make the launch of his career unforgettable. However, Fallon didn’t expect how awkward things would become. De Niro, known for his few words, didn’t make things any easier. In no time, the interview turned into a challenge, with De Niro giving mostly one-word answers to Fallon’s questions.
Fallon felt the pressure during his first big interview and struggled to keep the conversation going. He later admitted to The Things, “It was flop sweat pouring down my face. My hair looked like I had a comb-over... At one point, I couldn’t even see him—I was just getting loopy.” Nervous and awkward, Fallon tried, but failed, to keep the interview from falling flat. Things took a turn for the worse when he realized De Niro wasn’t promoting anything and had little to say. Fallon awkwardly ran out of questions, even joking that he felt like he was “getting loopy” and couldn’t see De Niro clearly. Despite the tension, Fallon laughed it off later, admitting he had no idea what he was doing. “I sent you like 15 questions, and you go, ‘Pretty good, what else you got?’” Fallon recalled, laughing. “Now my questions are getting bizarre.” As he typed, he received an email from De Niro that simply read, ‘Ha ha, just kidding. See you on the show.’”
Fallon can now look back on that appearance with more humor after the years have passed. He admits just how nervous he was and wasn’t prepared for De Niro’s quiet, almost prankish demeanor. Surprisingly, De Niro was kind about the whole thing, telling Fallon he did a fine job, even though the actor rarely does interviews. That awkward moment became a memory Fallon still chuckles at, especially since it was his first big celebrity interview. “I gotta say, I had no idea what I was doing,” Fallon admitted after the rough interview, as per Time. “I ran out of questions to ask because you don’t even like doing talk shows that much.”
Jimmy Fallon’s road to late-night talk show host began when he was a teenager living in Saugerties, New York. In an interview with USA Today, he revealed how his mother noticed that he was always doing impressions and threw out the idea of entering some kind of local contest to see who could do the funniest impressions. Fallon decided to try it, performing different celebrity voices, including John Travolta and Jerry Seinfeld. He won the contest and took home $500, a big deal at the time for him. This gave him the confidence to pursue comedy as a career.
“I would do Seinfeld, and I did like 12 impressions in two minutes and I won the contest. I won a lot of money — I want to say, like, $500. So for two minutes of work — and I had been working since I was 13 — that was so much money. I freaked out and said, “This is my future! This is it!,” he said. He started doing stand-up shows, infusing his performances with humor and music. In college, he even opened for other comedians.
After graduating, he sent a videotape of his performances to potential agents. A manager in Los Angeles saw his tape and showed interest in working with him. This led Jimmy to make the move to LA, kicking off his comedy career and eventually landing him his iconic role as a late-night host. He has been the host of ‘The Tonight Show’ since 2014 and now, Fallon has just signed an extended contract that will take him at least through 2028 as the show’s host. With this, viewers can continue to expect Fallon to bring his fun, light-hearted style to the show for several more years.