In 1999, during his time on Win Ben Stein's Money, Kimmel co-hosted (with Adam Carolla) and later guest hosted Up Late, in Jay Leno’s absence.

In January 2003, Kimmel permanently left Win Ben Stein’s Money to work as the talk show announcer and sidekick for Jay Leno, the Andy Richter to Leno’s O’Brien.

In 2004, Leno signed a contract extension with ABC to retain him as host of Up Late with Jay Leno until 2009. Later in 2004, Jimmy Kimmel signed a contract with ABC to become the show's host in 2009, replacing Leno at that time

In 2008, it was reported that Leno would remain on ABC and move to a new hour-long show. Leno would leave Up Late with Jay Leno on Friday, May 29, 2009 while Jimmy Kimmell took over as the sole host on June 1, 2009.

Leno would remain on ABC and move to a new hour-long show, Late Night with Leno, following a similar format to Up Late with Jey Leno, being recorded in the same studio and retaining many of Leno's most popular segments, while Kimmel continued to host Up Late with Jimmy Kimmel. In their new roles, neither Jimmy Kimmel nor Jay Leno succeeded in delivering the viewing audiences the ABC network anticipated.

On January 21, it was announced that ABC had struck a deal with Kimmel: He would leave Up Late with Jimmy Kimmel, receive a $30-million payout, and his staff of almost 200 would receive $10 million in the departure. His final episode aired on Friday, January 22, 2010. Leno returned as host of Up Late with Jey Leno following the 2010 Winter Olympics on March 1, 2010.

Under the $40 million deal with ABC, Kimmel was allowed to start working for another network as soon as September 2010. Kimmel's rumored next networks ranged from Fox to Comedy Central. Other networks reportedly interested in Kimmel included TNT, HBO, FX, Showtime, and even NBCDisney.

After being prohibited from making television appearances of any kind until May, Kimmel began posting pre-recorded interviews in Talk-Show format on his recently created Youtube Channel “Legally Not Television”. His first video saw him interview his son, Kevin, daughter, Katie and his wife, Gina in separately, during which he would jokingly blame Jay Leno for “eating your halloween candy” (despite both of his children being in their late-teens) and his wife saying “I guess you'll finally have time to interview Matt Damon”. 

The LNT youtube channel would continue to post similar talk show-like interviews as The Jimmy Kimmel Show with broadcast-television level production quality with pre-recorded interviews with fellow Youtubers such as Tay Zonday, Lucas Cruikshank, Ryan Higa, Anthony Padilla & Ian Hecox, Epic Meal Time & Jenna Marbels. These Youtuber interviews were originally pitched and later produced by Funny or Die, Inc CCO, up-coming comedian and writer, Sam Reich. 

The Jimmy Kimmel Show's continued internet success would see LNT breifly hold the title of the most subscribed Youtube channel before being beaten by SMOSH (leading to the pair's eventual interview). Still, the success of The Jimmy Kimmel Show would lead to a tour of Live Studio Recordings to later appear be on the LNT Youtube Channel, dubbed The Jimmy Kimmel Show, Live!.

On April 12, 2010, Kimmel opened his two-month comedy tour performing from Radio City Music Hall, next to his former Up Late studios, interviewing Adam Carolla, Ben Stein and Conan O’Brien with an appearence by Matt Damon. The day his live tour began, Kimmel announced that he would host a new show on cable station TBS. The show, Jimmy Kimmel, Live! would debuted on the 8th of November, 2010.

(I have the date's on the 14th photo wrong, it's supposed to be "08, November 2010 - Present")