- Milestone Celebration:
- For the 10th anniversary show in 2013, Matt Damon staged a Hostile Show Takeover, renaming the show Jimmy Kimmel Sucks!. Jimmy Kimmel was tied up, gagged, and relegated to the background, while Matt interviewed various people who all proclaimed their hatred for Jimmy.
- The 20th anniversary show in 2023 had George Clooney, Snoop Dogg, and Coldplay, who were all Jimmy's first guests, appearing again. Jimmy also interacted with a digitally-recreated incarnation of himself from 2003.
- Throw It In!: How the Signing-Off Catchphrase "Apologies to Matt Damon, we ran out of time!", and by extension, the entire Jimmy/Matt feud started. As Jimmy Kimmel Live! started in 2003, the show was having trouble finding its voice. After one night which Jimmy believed was very weak, he ad-libbed the line, which was amusing to both the audience and Damon himself.
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