After retiring from cricket, Ankola shifted his focus towards entering films. He made his cinematic debut through the 2000 Hindi film "Kurukshetra", where he played the role of a cop accompanying his senior officer played by Sanjay Dutt. He followed that with "Pitaah" (2002), and his last major release "Chura Liyaa Hai Tumne" (2003) featured him alongside Esha Deol and Zayed Khan. The following year he acted in "Silence Please...The Dressing Room", where he played the character of a cricket captain. The film did not fare well at the box-office, nonetheless Ankola's performance was highly appreciated. He also participated in the first season of "Bigg Boss", Indian version of the reality show "Big Brother" in 2006. Prior to that, he acted in the Indian soap opera titled "Karam Apna Apna", where he signed a contract with Balaji Telefilms that " would not act in any television show on any channel apart from those produced by Balaji Films". Since he appeared in "Bigg Boss" before the contract would expire—one year from June 2006—the Bombay High Court ordered him not to act in any TV shows on other channels that are considered rivals for Sony Television. "Ssshhhh...Koi Hai" and "Kora Kagaz" are some of the other soap operas that he has acted. In 2008, it was reported that Ankola has been suffering from depression and was enrolled in a rehabilitation centre in Pune. The reason behind the illness was believed to be his severe addiction to alcohol. As a result of this his wife decided to settle with her parent in Pune with their children, leaving Ankola isolated.