Jimmy Kimmelis on a two-month break, and this August, his fans can look forward to Rosie O’Donnell temporarily taking over the hosting duties.
It looks like O’Donnell is already planning for her week on Jimmy Kimmel Live! The comedian recently posted a photo on Instagram of Rihannaand A$AP Rocky with the caption, “I’d love to interview u on Kimmel – the week of Aug. 17!” So now fans know two things: 1. Rosie will guest host Kimmel from August 17 through the 21st, and 2. She really wants Rihanna to appear on the show.
While the ‘Umbrella’ singer hasn’t responded publicly (yet), plenty of Rosie’s friends, fans, and fellow celebs have commented on her post. Trump supporter and actor Stephen Baldwin chimed in with “What about me?” But Jimmy may not approve.” Of course, both Kimmel and O’Donnell vehemently oppose Trump, and neither has had a problem showing it.
Prior to leaving for his break, Kimmel said (while announcing his guest hosts), “And for a special treat for our commander in chief, I asked one of his all-time favorites, Rosie O’Donnell, to be here to keep the hits coming.” He continued, “You’re welcome, and all I ask in return, Mr. President, is that you don’t do anything stupid while I’m gone.”
Rosie isn’t the only one who would love to see Rihanna on Kimmel. Commenters replied to her post with, “That would be amazing”, “Shoot your shot Rosie”, “Love her almost as much as you. I’d love to see you interview her. You have always been so amazing interviewing,” and, “Iconic if she returned for Rosie’s return. Ri & Ro.”
Even though most of the comments were all for a Rihanna-and-Rosie show, some (other than Stephen Baldwin) had a few ideas of their own. One commenter wrote, “You should interview Matt Damon,” while others suggested Madonna, Tom Cruise, or Kathy Griffin.
Some of Rosie’s fans went a step further, crossing their fingers and hoping that this could become a permanent position (even with a different network): “Wish HBO would give you a show akin to Last Week Tonight. I would tune in.”
So, will she or won’t she? Despite the pleas from Rosie’s fans for Rihanna to comment on the post, the Grammy Award winner has kept mum. But there’s still time for her to decide. In the meantime, Anthony Anderson, Ike Barinholtz, Colman Domingo, and Jelly Roll will get their turns hosting Jimmy Kimmel Live!
This story was originally published by Parade on Jul 13, 2026, where it first appeared in the Celebs section. Add Parade as a Preferred Source by clicking here.
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