Inside Jimmy Kimmel’s On-Air Tears: Why This One Was His Hardest

Jimmy Kimmel is usually the guy who finds the joke in any situation. Not this time. On his show, he broke down while paying tribute to his friend and bandleader, Cleto Escobedo III, who died at 59. It was raw, heartfelt, and clearly the hardest thing he has had to say on TV in a long time.

Kimmel remembers Cleto Escobedo III

Kimmel and Cleto were not just co-workers; they go way back. As Kimmel told it, they became friends when he was 9. Cleto inherited music from his dad, Cleto Escobedo Sr., a serious player in his own right. When ABC handed Kimmel his late-night show, he made sure both Cleto and his father were part of the band from the jump.

"We have been on the air for almost 23 years, and I have had to do some hard monologues along the way. But this one is the hardest because late last night, early this morning, we lost someone very special who was much too young to go, and I would like to tell you about him. If you do not mind."

He also took a beat to remind everyone watching to hold on to their people while they can. It was simple and sincere, and it landed.

The other heavy monologue: free speech and a messy backstory

Kimmel has done serious before. The most recent example he pointed to was a monologue about free speech that followed a dust-up where 'Jimmy Kimmel Live!' was taken off the air by ABC after he made a controversial comment related to talk about conservative influencer Charlie Kirk being assassinated. When the show returned on September 23, he came out swinging about what free speech means to him.

"Our freedom to speak is what they admire most about this country, and that is something I am embarrassed to say I took for granted until they pulled my friend Stephen off the air, and tried to coerce the affiliates who run our show in the cities that you live in to take my show off the air. That is not legal. That is not American. That is un-American."

He also clarified that he did not intend to degrade or offend anyone in connection with Kirk’s death; he said he only wanted to talk about it. Quick clarity check here, because this part is confusing: Charlie Kirk is alive, and the alleged suspension specifics have not been independently confirmed by ABC. The point, though, is that Kimmel framed the return episode as a free speech moment and made it very clear where he stands.

Why this one hit different

Kimmel has had plenty of emotional nights, but losing Cleto is personal in a way that is obvious even if you have never watched a full episode. This was a decades-long friendship that became the backbone of his show. If you have tuned in at any point over the last 23 years, you have felt Cleto’s presence, even if you did not know his whole story until now.

• Show: Jimmy Kimmel Live!
• Host: Jimmy Kimmel
• Seasons: 24
• Network: ABC
• Streaming: Hulu (US)