D.B. Sweeney
D.B. Sweeney plays the one of the eight White Sox players who were out of baseball after allegedly throwing the World Series. The stats of Jackson tell a completely different story, but that hardly mattered in the rush to shift the blame from owner Charles Comiskey onto the poorly paid players. There was a problem, however: Shoe Joe Jackson was arguably the best left-handed hitter in the game in 1919 and D.B. Sweeney is right-handed. To learn how to hit left-handed, Sweeney spent some time with a Class A minor league team.
John Cusack
Chicago native Cusack was still a year away from his defining role in Say Anything. Like many of the other actors, director John Sayles hired Cusack not only because he was part of the New Wave of up and coming young actors either part or associated with the “Brat Pack” but because of his baseball playing skills.
David Strathairn
Strathairn was originally going to play Shoeless Joe Jackson, but wound up playing one of the truly guilty members of the Black Sox. Cicotte did take money and did perform poorly in the World Series, but he also probably had the single greatest justification. Cicotte was guaranteed a a bonus bigger than his yearly salary if he won 30 games that season; with 29 wins and the opportunity to pitch again before the postseason, White Sox owner Charles Comiskey ordered him benched on the flimsy excuse of saving his arm for the World Series. Strathairn provided the perfect mix of greed and regret to make Cicotte one of the most memorable characters in the film's large ensemble cast.
John Mahoney
John Mahoney was considerable older than most of his co-stars, yet at about the same point in his career as most of them as well when he took on the role of the White Sox manager. He would reteam with one on the kids a year later in what would also prove to be something of a breakout role for him, playing the father of the young woman whom John Cusack famously serenades with a boombox playing Peter Gabriel in Say Anything.
Charlie Sheen
Eight Men Out would be the first of back-to-back movies where Charlie Sheen played a baseball player. While critically lauded, Eight Men Out was not a box office hit. The same cannot be said of Sheen’s follow-up: Major League.
Michael Lerner
Lerner was the fourth actor to play legendary underworld figure Arnold Rothstein and, according to legend, the real-life figure upon whom The Great Gatsby character Meyer Wolfsheim is based. In addition to Lerner, Rothstein has been portrayed by David Janssen and F. Murray Abraham.
John Sayles
The film's writer and director plays America's first famous sportswriter, Ring Lardner in the film.
