WARNING: SPOILERS ahead for Hacks season 4, episode 6.

Rosie O'Donnell's surprise guest appearance in Hacks season 4 guest stars. O'Donnell shares a few scenes with Jean Smart's Deborah Vance and introduces her to accept the "Courage in Comedy" award, which Deborah sees as a network stunt to help boost her late-night ratings.

After Hacks season 4, O'Donnell is expected to play Mary in And Just Like That... season 3, which premieres on HBO and MAX on May 29, 2025. During her first scene with Deborah in Hacks season 4, episode 6, the two laugh like old friends as Rosie jokingly calls Deborah "The bravest woman in comedy." Similar to Carol Burnett's Hacks cameo in season 4, episode 4, O'Donnell offers Deborah some advice about celebrating "every little win" in the "tough town" of Hollywood. Still, the helplessly candid Deborah can't help but see it as a fake award, which O'Donnell its she has plenty of herself.

Rosie O'Donnell's Hacks Season 4 Cameo Arrived 3 Years After Her Official Podcast Appearance With The Creators

She Was A Self-Proclaimed "Superfan" Of Hacks Back In Season 2

Before her season 4 cameo, Rosie O'Donnell entered the Hacks universe as a special guest and self-proclaimed "superfan" of the show on The Official Hacks Podcast. In an interview and Hacks season 2, episode 6 recap with series creators Lucia Aniello, Paul W. Downs, and Jen Statsky, O'Donnell ed as a guest host to discuss the episode, titled "The Click." Downs reveals at the start of their conversation that O'Donnell has personally reached out to the Hacks creators to share how much she enjoyed and even connected to the show back then, which is still evident based on her season 4 cameo.

Considering all the that O'Donnell had to offer Hacks back in season 2, it's a bit surprising that it took this long for her to get a cameo. However, it makes sense that O'Donnell would appear in season 4, which has some of the biggest guest stars in the show's history thus far, such as Kristen Bell, Jimmy Kimmel, and Merrill Markoe. O'Donnell also appeared as herself on the celebrated HBO showbiz comedy show Curb Your Enthusiasm starring Larry David several times throughout its 12-season run. She was also cast in other recent critically acclaimed series such as Russian Doll and I Know This Much Is True.

Rosie O'Donnell's Hacks Cameo Has A Deeper Meaning In Deborah's Story

O'Donnell Was A Legendary Trailblazer For Female Hosts On Television

Rosie O'Donnell's guest appearance in Hacks season 4, episode 6 continues a trend that began with Carol Burnett and Merrill Markoe's appearances earlier in the season. Like Burnett, the host of the iconic and progressive "The Carol Burnett Show", and Markoe, the prolific head writer on Late Night with David Letterman, O'Donnell was also a trailblazer for women in the entertainment industry. As a dominant female TV host back in the '90s and '00s, O'Donnell's presence in Hacks also honors her legacy. While Deborah is a fictional character, she represents these icons who paved the way for women in TV.

Although Deborah has had success in entertainment as a stand-up comedian and entertainer, her lifelong dream is to host a late-night show, which she finally accomplished in what many would call the twilight of her career. No one in reality has achieved what Deborah has in the fictional world of Hacks, with all the mainstream late-night shows being hosted by men for decades, although Taylor Tomlinson recently broke ground with her game show, After Midnight.

When Deborah was in her twenties, she had the opportunity to host a late-night show ripped from her based on her ex-husband's defamatory lie.

When Deborah was in her twenties in the 1970s, she had the opportunity to host a late-night show ripped from her based on her ex-husband's defamatory lie. Having figures like Burnett, Markoe, and O'Donnell in Hacks honors their collective real-world impact.