Sheen and father Martin Sheen, a Dayton native, were at the Reds game against Pittsburgh on Friday and saw Brennaman get his head shaved. Brennaman had promised to shave his hair if the Reds won 10 consecutive games and said he would do it publicly if fans donated at least $20,000 to the Reds fund.
That drive generated $50,000, and Charlie Sheen announced Sunday he planned to match that amount.
"The City of Cincinnati has opened its arms to me so graciously and I'm compelled to give something back," Sheen said in a statement released by the Reds. "If this contribution points one kid in the right direction, then we've done our job."
The Sheens were at Great American Ball Park for the weekend series between the NL Central-leading Reds and the second-place Pirates and were celebrating the birthday of Martin, Charlie's father.
Charlie portrayed relief pitcher Ricky Vaughn in the 1989 movie "Major League" and threw on the field before Saturday's game.