Beating out Cage in Leaving Las Vegas? Yeah, I’d go with that.
Penn’s got some quality movies & performances spread out over the years. Carlito’s Way, Mystic River, and Milk are other very good ones to catch if you haven’t already.
In the DVD commentary for Mystic River, Kevin Bacon and Tim Robbins are talking about how intense Penn was in one scene in particular (the one where he’s being held down by police). Robbins, an an Academy award winner himself for that film, said he thought Penn was going to have a heart attack (or something similar) due to his intensity in that scene. Bacon laughed, agreed, and said something like, “Oh god yeah for sure. He really brought it.”