programmer Jim Sting in WarGames and prosecution witness Sam Tipton in My Cousin Vinny. In 1990, he had a small but pivotal role in the film Dances with Wolves, portraying Major Fambrough, an Army fort commander who kills himself as a result of becoming insane. Chaykin had his first starring role in Whale Music, a 1994 film in which he played a burned-out rock star, a character based largely on Brian Wilson. Chaykin was named Best Actor at the 15th Genie Awards for his portrayal. Chaykin also had roles on the television series Seeing Things and Emily of New Moon as well as a recurring role as the intergalactic gourmand Nerus (a nod to Nero Wolfe) in Stargate SG-1. Chaykin portrayed the colorful bookie Frank Perlin opposite Philip Seymour Hoffman's compulsive gambler Dan Mahowny in Owning Mahowny, a film that critic Roger Ebert named as one of the ten best of 2003. In 2006, Chaykin appeared in an episode of the Ken Finkleman miniseries At the Hotel and received a Gemini Award for best performance by an actor in a guest role. He had a semi-recurring role in the HBO series Entourage, as volatile movie producer Harvey Weingard, a send-up of the disgraced producer Harvey Weinstein. He also appeared as Stan Deane, father of Kevin Zegers' character Woody Deane, in the 2006 romantic comedy It's a Boy Girl Thing. Chaykin starred as Sam Blecher, the owner of a family-run driving school in Winnipeg, in the first two seasons (2008–2010) of the Canadian comedy-drama television series Less Than Kind. The series received the 2010 Gemini Award for Best Comedy Program or Series. "Sam is an out-of-control, good-hearted, big-hearted person who just can't quite get it right with his family," Chaykin told Q radio interviewer Jian Ghomeshi in April 2010. "He's full of love but he can't express it. But what he does express is anxiety, desperation, and the need to dominate, which is kind of pathetic." Asked whether he liked the character, Chaykin replied, "I love him. I do, I really do, and it's the same kind of love that a person has for family — where you see their foibles but at the same time you embrace them because they are a part of you. And Sam certainly is a part of me." In 2011 Chaykin posthumously received the ACTRA Toronto Award for Outstanding Performance — Male for his performance