Two things typically associated with Bill Simmons are Boston and basketball. So the first two guests for his new HBO show, Any Given Wednesday with Bill Simmons, probably shouldn’t be a surprise.

As first reported by The Hollywood Reporter‘s Lacey Rose, Charles Barkley and Ben Affleck will be Simmons’ first interviews on his debut program. Barkley will appear in the show’s first segment, which is supposed to focus on a particular topic. Considering that the NBA Finals will have concluded on Sunday, it’s a fair guess that Simmons and Barkley will discuss the series, the various storylines that developed and the results of Game 7.

Simmons’ second guest will be Ben Affleck. As mentioned in THR‘s June 8 profile, these interviews are expected to last 10 to 12 minutes and feature a wider-ranging conversation much like what would Simmons have on his podcast. Boston sports — particularly the Red Sox — will almost certainly be discussed, but Affleck’s acting and directing career are pertinent topics as well. Will they discuss the negative reception toward Batman v Superman or the Sad Affleck meme?

Both interviews will be pre-taped, though Simmons intends for them to be recorded the day before airing. The segments will also be edited down from what Simmons hopes are much longer conversations. A few eyebrows have been raised over Simmons not doing the interviews live or in front of a studio audience. But as he explains it, the intention is to get something close to what he does on his podcast, which is a one-on-one conversation. Not only would talking in front of an audience be different from what Simmons has previously done well, but reaction could influence what gets discussed or how both Simmons and his guest behave.

The June 8 THR feature reported that Simmons wants to pair two guests in the interview segment — for instance, having Aaron Rodgers and Tony Romo discuss the difficulties of playing quarterback in the NFL — and he tried to get Affleck buddy Matt Damon to be a part of the conversation, but schedules couldn’t work out.

But for the first show, a huge sports personality and big celebrity are two quality, high-profile guests for Simmons. Will he be able to maintain that level of booking or, as former HBO president Michael Lombardo advised, will Simmons just focus on having insightful, engaging interviews and occasionally open eyes with a surprisingly big name. And will Simmons manage to get Michelle Obama, whom he’s named as his top choice, on the show eventually?

Any Given Wednesday with Bill Simmons premieres on HBO June 22 at 10 p.m. ET.

[The Hollywood Reporter]

About Ian Casselberry

Ian is a writer, editor, and podcaster. You can find his work at Awful Announcing and The Comeback. He's written for Sports Illustrated, Yahoo Sports, MLive, Bleacher Report, and SB Nation.

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