Fine began his career as a critic at 18, writing reviews of rock concerts and albums for the Minneapolis Star while a freshman at the University of Minnesota. He subsequently created entertainment sections at several of the newspapers where he worked. He conducted the Playboy Interview with Howard Stern and Tim Robbins for Playboy Magazine. Fine directed a documentary short, "Flo Fox's Dicthology," that was selected for the Woodstock and Amsterdam film festivals in 2002. His documentary feature, "Do You Sleep in the Nude?," about film critic Rex Reed, was selected for the Hamptons Film Festival and the South by Southwest Film Festival. His documentary, "," about comedian Robert Klein, had its debut at the 2016 South by SouthwestFilm Festival and subsequently played at Tribeca and the San Francisco Jewish Film Festival. It premiered on the Starz network in March 2017. Fine is a four-time former chairman of the New York Film Critics Circle: 1992, 2002, 2006 and 2015. He was named general manager of the NYFCC in 2016. He is a contributing editor for Cigar Aficionado magazine, for which he writes cover stories. He helped create and hosted the Journal-News Film Club at the Jacob Burns Film Center in Pleasantville, NY, from 2001 to 2004. Fine subsequently created, produced and hosted the Emelin Film Club at the Emelin Theater in Mamaroneck, NY, which began in 2005, until 2014. He launched the Thalia Film Club at Symphony Space on Manhattan's Upper West Side in 2010. He was named critic-in-residence at in Pelham, NY, in 2014, where he produces and hosts The Picture House Film Club. On July 16, 2012, he provoked anger when he posted the first negative review of The Dark Knight Rises. His review was posted on review site Rotten Tomatoes and within minutes, started receiving hateful comments and death threats. Rotten Tomatoes had to remove the link to his review and temporarily disable comments on reviews for the movie. When asked about the situation in an interview, he said "It's part of the job." He published his first novel as an e-book, entitled Killing My Idiot Boss. He is a founding member of Westchester Collaborative Theater, and has written several plays – one-act and full-length – produced by the company.
