Caitlyn Jenner GLAAD Awards

Caitlyn Jenner, Former Olympic Star As Bruce, To Join Bill Simmons’ HBO Show

Like a Boston Red Sox season with high expectations, things have not started off pretty for Bill Simmons and his new HBO show, Any Given Wednesday. Not only have ratings been ugly, but critical reception has been less-than-stellar and the show, after just a month, has seemingly dug its own hole and is following in the footsteps of a former HBO show in Joe Buck Live.

But, if there’s one thing that Bill Simmons and HBO have in common (besides a love for cursing), it’s that they don’t give up when the times get rough. In a press release released to the media on Wednesday afternoon, HBO announced the following for this week’s episode of ‘Any Given Wednesday.’

“ANY GIVEN WEDNESDAY WITH BILL SIMMONS, a weekly talk show hosted by one of the most influential figures in contemporary sports media, continues its 20-show season WEDNESDAY, AUG. 3 (10:00-10:30 p.m. ET/PT), followed by other new episodes subsequent Wednesdays at the same time, exclusively on HBO. This week’s show features a one-on-one interview with Caitlyn Jenner, who competed for the U.S. Olympic Team as Bruce Jenner in 1976, winning the gold medal in the decathlon. NBA player J.J. Redick and actor Lamorne Morris will join Simmons for a panel discussion.”

If you want to bring in the viewers and get people talking, landing a one-on-one interview with Caitlyn Jenner is a good start. Jenner, who was born Bruce, underwent a controversial sex change procedure in 2015 and has become a face for the LGBT community in the months since. Of course, this has come with hatred and transphobia from fans who adored and respected her as Bruce, the Olympic star that loved running but eventually went on to realize she was a woman inside.

Bruce Jenner, Caitlyn Jenner
[Photo by AP Photo]
After years of crossdressing and being jokingly called a woman (most notably by Family Guy, who actually predicted the sex change in a 2009 episode), Jenner underwent sex change surgery in the spring of 2015 and was instantly called a hero and a brave woman for following through on her dreams. In fact, she even won the Arthur Ashe Courage Award at the 2015 ESPYS, turning the internet into a warzone in the process.

Not all has been good for the former Olympic star as of late, however, as she has battled issues with her family that likely stem from her sex change and recently saw her television series, I Am Cait, cancelled by E!, as the Inquisitr announced yesterday. Radar‘s Gina Bacchiocchi reported the following on Wednesday morning that supposedly came from a source/insider close to the Jenner/Kardashian family.

“It’s really bad between Caitlyn and the kids right now. They still feel she hasn’t handled the transition well with them at all. Nothing has been resolved. The girls still feel abandoned and betrayed. It’s a sad situation… Caitlyn underwent many surgeries right away, and the whole process has been very difficult for her, physically and emotionally. Sadly, she doesn’t feel like she can confide in anyone during her time of need.”

Simmons can most likely relate to Caitlyn about being in a time of need, as the former ESPN star has struggled with ratings and positive feedback for the first month of his highly-anticipated HBO show. While slow ratings may have been expected with the start of a new show, well, @SportsTVRatings can probably describe it best.

Yikes. When you’ve only hit 300,000 viewers once in the middle of July — a time when the only sport on that people are actually watching is baseball — then it’s pretty apparent that things are not going well. Keep in mind, this was arguably the most anticipated show on television since FOX’s Gotham, especially after how Simmons ended things with ESPN in 2015.

Bill Simmons Vanity Fair
[Photo by Mike Windle/Getty Images for Vanity Fair]
But, there are reasons to remain optimistic if you’re a fan of Simmons’ show — or, if you’re someone at HBO who is internally worried if this was a mistake or not. First, Simmons himself has not been the reason why the show has struggled with ratings — all of the wit, bravado, and humor we’ve come to expect from the lifelong Boston fan is there, especially when he tackles topics like Roger Goodell or how corrupt the NFL is. This is not an example where the host is either critically out of his league or lacks interesting, unique ideas that would cause viewers to watch — just look at last week’s episode with the Michael Rapaport, Judge Joe Brown, and the DeflateGate trial!

The other reason to remain optimistic is that Simmons has struggled with adversity before, and HBO is dedicated to proving that a sports talk show can work. Really, all that needs to be done is the idea of moving the show to a better time slot (many have suggested Sunday nights, immediately after Ballers) and not having Simmons relying so much on guests. The show has mainly been hit-or-miss so far, yes, but hit-or-miss in terms of the content is much better than bombing miserably.

Tonight’s show, by having a one-on-one interview with Caitlyn Jenner in a time where she is utterly miserable, will be a good test of character for both Simmons and the show. If the interview goes well, optimism will rightfully be raised for Any Given Wednesday, but if not? Well, maybe that’s not something we should think about just yet.

Other HBO air dates include Aug. 4 (12:45 p.m., 3:05 a.m.), 5 (10:15 a.m., 1:05 a.m.) and 7 (11:00 a.m.), while HBO2 playdates are currently set for Aug. 3 (11:00 p.m.), 4 (9:00 a.m.), 6 (11:00 a.m.), 8 (3:20 a.m.), and 9 (12:30 a.m.). For up-to-the-minute updates about Any Given Wednesday, follow on Twitter at @AnyGivenWeds or join the conversation using #AnyGivenWednesday.

[Photo by Rob Kim/Getty Images]

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