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Denis Leary

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Episodes featuring their films
2
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2

Rewatchables episodes featuring their films

The Sandlot poster

The Sandlot

1993 film

Bill Simmons · Mallory Rubin · Mina Kimes

Aired August 4, 2020

Draft Day poster

Draft Day

2014 film

Bill Simmons · Mallory Rubin

Aired May 14, 2020

Displaying all 2 episodes

Mentioned in discussions

The Departed poster
The Departed

Casting What-Ifs

Brad Pitt as Sullivan; Al Pacino as Costello; Ray Liotta or Denis Leary as Dignam; Mel Gibson as Ellerby; Robert De Niro as Queenan

In the discussion (10)
Approx. transcript time · 01:13:42Read transcript
  • The casting what-ifs are called probably the best for any movie they have done, a whole alternate Departed.
  • Pitt bought the producing rights, planned to play the Damon part, then decided he might be too old and went to do Babel.
  • Debate over Pitt: good instincts about roles and a great producer, but miscast himself in Meet Joe Black and The Devil's Own; Damon was the better choice.
  • Scorsese wanted Al Pacino for Costello; Pacino turned it down and Nicholson was the second choice.
  • Ray Leota was the original choice for Dignam but declined over other commitments, his 2006 films including Comeback Season, Local Color and Even Money.
  • Dennis Leary was the second choice for Dignam but had to make season three of "rest of me" (as transcribed); he would have been great, though Walberg is perfect.
  • Ellerby was offered to Mel Gibson, who was starting Apocalypto; Queenan was supposed to be De Niro, who made The Good Shepherd; the Anthony Anderson role was meant for "the Rizza" (transcript form, unresolved), who was too old or had conflicts.
  • Leo was in The Good Shepherd but dropped out to play Billy Costigan, and Damon then took The Good Shepherd role; The Good Shepherd is called an unexamined movie with a dynamite cast.
  • The alternate cast (Leo, Pitt, Pacino, Leota, De Niro, Mel Gibson and the Riza) is called pretty loaded and preferred by one participant; Pacino would lose Costello's lumbering physicality but gain CR doing Pacino.
  • Would-you-rathers: Walberg over Ray Leota, Baldwin over Mel Gibson 100 out of 100 times, and De Niro over Sheen since he can underplay.
The Departed poster
The Departed

Casting What-Ifs

Reported or imagined alternatives: Brad Pitt, Ray Liotta, Denis Leary, Pacino, De Niro, Gibson, and RZA; uncertain Nicholson improvisation stories

In the discussion (8)
Approx. transcript time · 00:14:38Read transcript
  • Brad Pitt was reportedly set for the Damon part, dropped out, and produced instead.
  • Ray Leota was reportedly set for Dignam but could not do it.
  • Denis Leary was the next reported Dignam possibility and also could not do it.
  • Al Pacino was the first reported Costello choice and is debated as an alternate.
  • Robert De Niro reportedly declined Queenan to make The Good Shepherd.
  • Mel Gibson reportedly could not play the Alec Baldwin part because he was filming Apocalypto.
  • RZA was reportedly offered the Anthony Anderson role.
  • Nicholson’s proposed prostitute scene and retained dildo improvisation are presented with explicit uncertainty.
Displaying all 3 discussions

Films in the archive