Casting What-Ifs

Alternate casting possibilities.

Casting What-Ifs has run in 373 episodes. The most recent 40 are listed below — open any episode at its timestamp to hear the segment.

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‘Pacific Heights’Bill Simmons

Christopher Reeve lobbied to play Carter Hayes but lost out because Michael Keaton was cast (Keaton wanted the movie, being Batman at the time). Also picks Nobu McCarthy (Mrs. Watanabe/Karate Kid II) as favorite 'That Guy' choice, and separately names Luca Bercovici (Muzzin in American Flyers) as his 'That Guy' category winner.

‘Pacific Heights’Chris Ryan

Picks Dorian Harewood as winner of the 'That Guy' category because he played Eightball in Full Metal Jacket alongside Modine.

‘Pacific Heights’Kyle Brandt

Notes it's cool that the casting choice came down to Superman (Reeve) or Batman (Keaton). Separately picks Hal Landon Jr. (the balding officer/locksmith scene, also Ted's dad from Bill & Ted) as his 'That Guy' pick.

‘The Good Son’Bill Simmons

Notes that in 1988 the movie was almost made with Michael Klesick as Henry, Jesse Bradford also considered, Mary Steenburgen as the mom, and Michael Lehman (Heathers director) as director; also debates whether Wendy Crewson counts as a 'that guy' due to roles in The Good Son and The Santa Clause

‘The Good Son’Chris Ryan

Speculates that a Michael Lehman-directed version would have had more tongue-in-cheek black comedy

‘The Good Son’Sean Fennessey

Agrees Lehman's other films suggest a darker comedic tone, but questions whether that tone would have worked for this movie

‘Domestic Disturbance’Bill Simmons

Proposed recasting the sergeant role in domestic disturbance with three choices: 50 Cent (post 'Get Rich or Die Tryin''), Philip Michael Thomas, and Ernie Hudson; ultimately says he likes Philip Michael Thomas the most

‘Domestic Disturbance’Sean Fennessey

Reacts skeptically to 50 Cent as the sergeant ('not sure he screams Maryland police lieutenant') and jokes about Laurence Fishburne playing the '8th lead' in domestic disturbance right after The Matrix

‘The Hand That Rocks the Cradle’Bill Simmons

Cybill Shepherd turned down the role of Peyton for feminist reasons; Bill says he's glad she didn't take it despite thinking she 'should have.' Also notes Christopher McDonald and Kevin Spacey were tested for Michael, and is thankful Spacey wasn't cast as it would have hurt the rewatchability. Suggests Christopher McDonald would have been good as Marty and jokingly proposes John de Lancie (Q from Star Trek) for a role.

‘The Hand That Rocks the Cradle’Chris Ryan

Floats the idea of a swap: Rebecca (Cybill Shepherd's Moonlighting co-star's role) playing Claire and Cybill Shepherd playing Peyton instead, saying 'that would have been' notable.

‘The Hand That Rocks the Cradle’Joanna Robinson

Jokes about the 'blonde on blonde' casting issue if Cybill Shepherd played Peyton alongside another blonde lead, questioning if you can have two blondes in one movie ('illegally blonde' joke); also gives Christopher McDonald a 'Best That Guy' award for his casting potential.

‘Single White Female’Van Lathan

Proposes recasting Bridget Fonda's lead role with Halle Berry (with the iconic Boomerang haircut), arguing it would add racial tension/complexity to the Single White Female premise; says Jennifer Jason Leigh's character wouldn't need to be recast.

Episode	Host	Answer
‘Pacific Heights’	Bill Simmons	Christopher Reeve lobbied to play Carter Hayes but lost out because Michael Keaton was cast (Keaton wanted the movie, being Batman at the time). Also picks Nobu McCarthy (Mrs. Watanabe/Karate Kid II) as favorite 'That Guy' choice, and separately names Luca Bercovici (Muzzin in American Flyers) as his 'That Guy' category winner.
‘Pacific Heights’	Chris Ryan	Picks Dorian Harewood as winner of the 'That Guy' category because he played Eightball in Full Metal Jacket alongside Modine.
‘Pacific Heights’	Kyle Brandt	Notes it's cool that the casting choice came down to Superman (Reeve) or Batman (Keaton). Separately picks Hal Landon Jr. (the balding officer/locksmith scene, also Ted's dad from Bill & Ted) as his 'That Guy' pick.
‘The Good Son’	Bill Simmons	Notes that in 1988 the movie was almost made with Michael Klesick as Henry, Jesse Bradford also considered, Mary Steenburgen as the mom, and Michael Lehman (Heathers director) as director; also debates whether Wendy Crewson counts as a 'that guy' due to roles in The Good Son and The Santa Clause
‘The Good Son’	Chris Ryan	Speculates that a Michael Lehman-directed version would have had more tongue-in-cheek black comedy
‘The Good Son’	Sean Fennessey	Agrees Lehman's other films suggest a darker comedic tone, but questions whether that tone would have worked for this movie
‘Domestic Disturbance’	Bill Simmons	Proposed recasting the sergeant role in domestic disturbance with three choices: 50 Cent (post 'Get Rich or Die Tryin''), Philip Michael Thomas, and Ernie Hudson; ultimately says he likes Philip Michael Thomas the most
‘Domestic Disturbance’	Sean Fennessey	Reacts skeptically to 50 Cent as the sergeant ('not sure he screams Maryland police lieutenant') and jokes about Laurence Fishburne playing the '8th lead' in domestic disturbance right after The Matrix
‘The Hand That Rocks the Cradle’	Bill Simmons	Cybill Shepherd turned down the role of Peyton for feminist reasons; Bill says he's glad she didn't take it despite thinking she 'should have.' Also notes Christopher McDonald and Kevin Spacey were tested for Michael, and is thankful Spacey wasn't cast as it would have hurt the rewatchability. Suggests Christopher McDonald would have been good as Marty and jokingly proposes John de Lancie (Q from Star Trek) for a role.
‘The Hand That Rocks the Cradle’	Chris Ryan	Floats the idea of a swap: Rebecca (Cybill Shepherd's Moonlighting co-star's role) playing Claire and Cybill Shepherd playing Peyton instead, saying 'that would have been' notable.
‘The Hand That Rocks the Cradle’	Joanna Robinson	Jokes about the 'blonde on blonde' casting issue if Cybill Shepherd played Peyton alongside another blonde lead, questioning if you can have two blondes in one movie ('illegally blonde' joke); also gives Christopher McDonald a 'Best That Guy' award for his casting potential.
‘Single White Female’	Van Lathan	Proposes recasting Bridget Fonda's lead role with Halle Berry (with the iconic Boomerang haircut), arguing it would add racial tension/complexity to the Single White Female premise; says Jennifer Jason Leigh's character wouldn't need to be recast.