Fallon landed his second audition at the age of 23. At the "notoriously difficult audition," he was told by several people that creator Lorne Michaels almost never laughed during auditions. He feared being outshined by the comic before him, who came armed with an arsenal of props. Despite this, Fallon went onstage and did well, performing a "celebrity walk-a-thon" with impressions of Jerry Seinfeld, Chris Rock, Bill Cosby, and Adam Sandler, an SNL alumnus who had recently left the show. Michaels and others laughed.
In his off-time, Fallon released a book comprising e-mail exchanges with his sister Gloria, titled I Hate This Place: A Pessimist's Guide to Life (1999), and played a minor role in the film Almost Famous (2000). During their time at SNL, Fallon and Horatio Sanz often drank together. Sanz has described himself and Fallon as "super-functioning alcoholics", and said, "They say that kind of goes hand-in-hand with SNL, some kind of substance-abuse issues, because it's so stressful you easily find yourself blowing off steam a lot." On one occasion, they spent a Friday night watching The Strokes perform a midnight show, staying up drinking until the early morning, despite having to do SNL that night. "We actually took what we thought being on SNL was, what people think is awesome about it, and we made it happen," said Sanz, who said that he and Fallon got in more than a few bar fights.
Fallon began to pursue a film career in 2004. He had spurned most major roles due to lack of time and disinterest in the dozens of scripts he read. He signed on for his first lead role in Taxi, a remake of a French film, after co-star Queen Latifah became attached to the project. He was also attracted to the film's action comedy tone, seeing comparisons with SNL alumnus Eddie Murphy's first big film, 48 Hrs. (1982).
In the fall of 2003, he split his time between shooting the film in Los Angeles and returning to New York City for SNL. With his contract ending, his sixth season at SNL was his last; Fallon signed off at the conclusion of the show's twenty-ninth season in May 2004.
Fallon began receiving fewer film offers. He had entered what he has called a "lost period", drinking more alcohol and beset by confusion over his next career moves. Fallon moved back east to New York, spending "a couple of years aimlessly knocking around." He wrote a screenplay during this time "about a guy in a goth band who has to pretend to be a country-music star."
To prepare for the role of a late-night host, Fallon toured college campuses and comedy clubs for eight months, where he tested out a new 50-minute routine. He also began watching the comedy of Chevy Chase, Dick Cavett, and Johnny Carson, as well as The Larry Sanders Show. In May 2008, Fallon was announced as the successor to O'Brien's Late Night.
Fallon was considered an odd choice for the job, both by executives at NBC (who "hated" the idea and predicted it to be a failure) and among the general public. This was alluded to in an early promo for the series: "You loved him on SNL! You hated him in the movies! Now you're ambivalent."
Fallon proved himself different from other late-night hosts, with more of a reliance on music, dancing, impersonations, and games. Between his own musical sensibilities and the recruitment of his house band, hip-hop collective The Roots, Fallon's incarnation of Late Night "evolved into the most deeply musical of TV's musical-comedy variety programs," with sketches in which he parodies Neil Young and Bruce Springsteen going viral online.
As of August 2013, Fallon was earning a salary of $11 million a year for his work on Late Night.
On April 3, 2013, following a period of speculation, NBC announced that Fallon would succeed Jay Leno, following the 2014 Winter Olympics, to become the sixth permanent host of The Tonight Show. Fallon and Leno sang a parody of the song "Tonight" about The Tonight Show together. Fallon's Tonight Show debut on February 17, 2014, on NBC's network engaged 11.3 million viewers.
In 2020, Fallon and pacifier company WubbaNub created limited-edition pacifiers based on the penguin and cow characters from his children's books.
On November 4, 2017, Fallon's mother Gloria died from undisclosed causes at the age of 68 at NYU Langone Medical Center. Scheduled tapings of the following week's Tonight Show episodes were canceled. One week later, Fallon paid tribute to his mother following that night's monologue, becoming emotional and calling her "the best audience".
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