Holmberg's Morning Sickness - Arizona Episode: August 5, 2025 – Entertainment Drill: List Of Celebs Who Had Falling Out w/Celebrity Friends

Arizona's premier morning radio show, Holmberg's Morning Sickness on 98 KUPD, hosted by John Holmberg alongside Brady Bogen, Bret Vesely, and Dick Toledo, delves into the turbulent world of celebrity friendships in the August 5, 2025 episode. Titled "List Of Celebs Who Had Falling Out w/Celebrity Friends," the episode offers listeners an engaging exploration of high-profile friendships that have soured over time.

Celebrity Friendship Breakups

1. Kylie Jenner and Jordyn Woods

Brady Bogen kicks off the discussion at [05:04] by highlighting the decade-long friendship between Kylie Jenner and Jordyn Woods. The friendship faced a dramatic downturn when Jordyn had a romantic involvement with Tristan Thompson, Khloe Kardashian's boyfriend.

Brady: "They're friends for a decade. Tell Jordan had sex with Khloe Kardashian's boyfriend, Tristan Thompson."
John Holmberg: Reacts humorously to Jordyn's public presence despite the fallout, saying, "She's all over TMZ in her bikini now. Like, people want to see her because she's got a thick ass for some reason."

2. Gwyneth Paltrow and Winona Ryder

Moving to [05:43], Brady mentions the fallout between Gwyneth Paltrow and Winona Ryder, two prominent figures in the 90s. Their close-knit bond deteriorated over personal differences, showcasing how even strong friendships can unravel.

Brady: "Gwyneth Paltrow and Winona Ryder. They were buddies in the 90s. Best friends. They also were dating best friends."

3. Matt Damon and Ben Affleck

At [05:54], the discussion shifts to the iconic friendship between Matt Damon and Ben Affleck. Brady attributes their fallout to professional jealousy, particularly citing their competition during the filming of "Shakespeare in Love."

Brady: "Ben Affleck. According to legend, the fallout happened when Gwynne and stole Ben from. When they were doing that Shakespeare in Love movie."

4. Seth Rogen and James Franco

Seth Rogen and James Franco's friendship faced strain following sexual misconduct allegations against Franco. Brady notes that Rogen distanced himself from Franco amidst the controversy.

Brady: "When the sexual misconduct allegations came out on Franco, Seth said he had no plans continuing."
John Holmberg: Expresses uncertainty about whether their friendship persisted, remarking, "I don't think they did. And he abandoned him."

5. Kathy Griffin and Anderson Cooper

At [06:56], Brady brings up the longstanding friendship between Kathy Griffin and Anderson Cooper, which ended after Griffin's controversial photo shoot. The fallout highlights how public actions can impact personal relationships.

Brady: "Kathy Griffin and Anderson Cooper, lucky friends for two decades. Co-hosted CNN's New Year's Eve festivities for 10 years. And AC dropped her after she did that photo shoot with."

John Holmberg: Adds a humorous take on their dynamic post-fallout, "Anderson always looks good. Always. And he's got that thing standing back there with that six head she's carrying around."

6. George Clooney and Adam Sandler

George Clooney and Adam Sandler's friendship comes under scrutiny with Clooney's recent Netflix film "J. Kelly," where Sandler portrays his manager. Brady suggests tension arose from Sandler's reluctance to embrace Clooney's acting range.

Brady: "George Clooney recently did a movie for Netflix called J. Kelly. He plays an actor and Adam Sandler plays his manager... He can range."
John Holmberg: Critiques Sandler's acting prowess, stating, "We've seen it. It's unfortunate."

7. Playboy's Playmate of the Month Competition

The episode also touches on Playboy's relaunch of its "Playmate of the Month" competition. Brady discusses the new format involving judges like Shannon Moakler and former Playmates, predicting inevitable drama reminiscent of shows like "America's Top Model."

Brady: "Playboy is relaunching its Playmate of the Month competition with judges including Shannon Moakler and some other former Playmates."
John Holmberg: Cynically remarks, "This ends terribly. I'm watching every minute of it. This cannot."

Host Commentary and Humor

Throughout the discussion, John Holmberg injects humor and personal opinions, often making light of the situations or poking fun at the celebrities involved. For instance, regarding the fallout between Kylie Jenner and Jordyn Woods, he jokes about the reasons behind public interest, tying it back to social media exposure and appearance.

John Holmberg: "You can be awful. And then you throw a bikini shoot together and end up on TMZ and people like, oh, she's back."

Similarly, his banter with Brady about the state of celebrity friendships and their public perceptions adds a relatable and entertaining layer to the conversation.

Conclusion

The episode wraps up with John Holmberg sharing personal anecdotes and teasing upcoming segments, maintaining the show's signature blend of entertainment and candid discussion. The focus on celebrity friendship breakups provides listeners with both insightful commentary and amusing observations, making for a captivating morning listen.

John Holmberg: "They're always put together. You got Kathy Griffin hanging around. She's cramping Anderson's silver fox style. Anderson always looks good. Always."

As the show concludes, the hosts tease future episodes and upcoming events, ensuring listeners remain engaged and eager for more content.

Holmberg's Morning Sickness continues to entertain and inform Arizona's morning commuters with its blend of humor, celebrity insights, and lively discussions, firmly cementing its place as the state's #1 Morning Radio Show.