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. While NBC and Leno claim there were private meetings with the WGA where there was a secret agreement allowing this, the WGA denied such a meeting. 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 strike-breakers on August 11, 2009, Leno was not on the list.
On April 23, 2009, Leno checked himself into 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 Leno's first in 17 years as host. Initially, the illness that caused the absence was not disclosed, but later Leno told People magazine it was for exhaustion.
Because Leno's show continued to lead all late-night programming in the Nielsen ratings, the pending expiration of Leno's contract led to speculation about whether he would become a late-night host for another network after his commitment to NBC expired. Leno left The Tonight Show on Friday, May 29, 2009, and Conan O'Brien took over on June 1, 2009.
Jay Leno's new show, titled The Jay Leno Show, debuted on September 14, 2009. It was announced at the Television Critics Association summer press tour that it would feature one or two celebrities, the occasional musical guest, and keep the popular "Headlines" segments, which would air near the end of the show. First guests included Jerry Seinfeld, Oprah Winfrey (via satellite), and a short sit-down with Kanye West discussing his controversy at the 2009 MTV Video Music Awards, which had occurred the night before.
In 2009, he donated $100,000 to a scholarship fund at Salem State College (now Salem State University) in honor of Lennie Sogoloff, who gave Leno his start at his jazz club, Lennie's-on-the-Turnpike.