The Tonight Show
Starting in 1986, Leno was a regular substitute host for Johnny Carson on The Tonight Show. In 1992, he replaced Carson as host amid controversy with David Letterman, who had been hosting Late Night with David Letterman since 1982 (which aired after The Tonight Show), and whom many—including Carson himself—expected to be Carson's successor. The story of this turbulent transition became the basis of a book and a movie. Leno continued to perform as a stand-up comedian throughout his Tonight Show tenure. In 1988, he received a contract extension with NBC itself. The July 1995 episode of The Tonight Show which featured an interview with Hugh Grant (who had been arrested for receiving oral sex in a public place from a prostitute) saw Leno rate higher than Letterman for the first time.
In 2004, Leno signed a contract extension with NBC to retain him as host of The Tonight Show until 2009. Later in 2004, Conan O'Brien signed a contract with NBC to become the show's host in 2009, replacing Leno at that time.
During the 2007–08 Writers Guild of America strike, Leno was accused of violating WGA guidelines by writing his own monologue for The Tonight Show. NBC and Leno claimed there were private meetings with the WGA where a secret agreement was reached allowing this; the WGA denied such meetings. Leno answered questions in front of the Writers Guild of America, West trial committee in February 2009 and June 2009, and when the WGAW published its list of strikebreakers on August 11, 2009, Leno was not on it.
On April 23, 2009, Leno checked himself in to a hospital with an undisclosed illness. He was released the following day and returned to work on Monday, April 27. The two subsequently canceled Tonight Show episodes for April 23 and 24 were his first in 17 years as host. The illness was not initially disclosed, but Leno later told People magazine that it was for exhaustion.
During the 2005 trial of Michael Jackson over allegations of child molestation, Leno was one of a few celebrities who appeared as defense witnesses. In his testimony regarding a phone conversation with the accuser, Leno testified that he was not asked for any money and there did not appear to be any coaching — but the calls seemed unusual and scripted.
As a result, Leno was initially not allowed to tell jokes about Jackson or the case, which had been a fixture of The Tonight Show's opening monologue in particular. But he and his show's writers used a legal loophole by having Leno briefly step aside while stand-in comedians took the stage and told jokes about the trial. These stand-ins included Roseanne Barr, Drew Carey, Brad Garrett and Dennis Miller. The gag order was challenged, and the court ruled that Leno could continue telling jokes about the trial as long as he did not discuss his testimony. Leno celebrated by devoting an entire monologue to Michael Jackson jokes.
