YMMV / Jimmy Kimmel Live!

• Ensemble Dark Horse: Guillermo started out as comic relief centering around being a Funny Foreigner. However, his natural charm quickly won over audiences and he became Jimmy's sidekick and a major draw in his own right, with celebrities flocking to talk to him for his red carpet segments.
• Heartwarming Moment:
  • During his otherwise tearjerking story about his son's heart condition, Jimmy offhandedly mentions that Matt Damon sent him support.
    Jimmy: I hate to even say it but even that son of a bitch Matt Damon sent flowers.
  • Even more heartwarming, however, is the name of Jimmy's son, William. The reason this is heartwarming? William is the English equivalent of the Spanish name Guillermo.
• Harsher in Hindsight: One episode featured a "Mean Tweets" feature specifically dedicated to Barack Obama, with the then-President reading out a series of tweets critical of him. The last one was from Donald Trump, calling him the "worst president ever." Obama responded, "At least I will go down in history as a President." Cut to 2016...
• Hilarious in Hindsight:
  • Jimmy's sign-off catch phrase, "Apologies to Matt Damon, we ran out of time", became a little more poignant in April 2018 during "Marvel Week", in which all the guests were actors from the Marvel Cinematic Universe, and Matt Damon actually appeared in Thor: Ragnorak earlier in the year.
  • When Damon hosted the show in early 2013, Reese Witherspoon was pulled in off the street with a gag of how her shopping bags were packed with bottles of wine and liquor. Just four months later, Witherspoon made headlines by being pulled over for a DUI and arrested after screaming at a cop.
• Tear Jerker: Jimmy is prone to Manly Tears, so when something bad happens, it hits incredibly hard.
  • The entire story of his son's birth and subsequent heart disease is just tragic to hear, even though he lets us know it has a happy ending. The way his voice cracks and he just can't talk when he reveals the heart disease is heartbreaking.
  • In the wake of the Las Vegas shooting in October 2017, Jimmy dedicated his entire monologue to the victims of the tragedy and called out lawmakers for being unwilling to protect citizens. He didn't tell a single joke throughout the entire monologue, saying that no matter how much he wanted to have fun and joke he refused to disrespect the victims like that.
  • After Kobe Bryant's tragic death in January 2020, Jimmy hosted a special episode that was merely a montage of Bryant's 15 prior appearances on the show, opening with a brief monologue where he talked about his friendship with Kobe and offering his condolences to Kobe's family as well as the families of all who died in the same helicopter crash.
  • After Bob Saget's sudden passing in January 2022, Jimmy begins the show paying tribute to him.