The Parenthood star confessed his love for the Hollywood A-lister during an interview with U.S. talk show host Ellen DeGeneres on Wednesday (16Apr14), revealing he began idolising for Pitt 20 years ago following his breakout role in 1994's Legends of the Fall.
Shepard explained, "I have really strong, strong feelings about Brad Pitt... Always have. I really am obsessed with him. He has great taste, I love all his movies, he's a phenomenal producer, he's a philanthropist and he's aging so gracefully."
The first time Shepard met Pitt was at the Oscars, where he accompanied wife Kristen Bell, who served as a presenter.
Shepard admitted, "I had never met him, nor did I even want to, because I'd be afraid I wouldn't be able to talk to him... (At the Oscars) Kristen starts pulling my leg, and she goes, 'He's talking to you. He's talking to you!'
"And I turn around and Brad Pitt is talking to me from four rows up! He goes, 'We love your movie.' And in that moment I completely forget that I've directed a movie (2012's Hit and Run) because I just forgot and I go, 'What?'"
After Pitt clarified his comments, Shepard gave a simple 'Thank you' and sat down, but the memorable encounter couldn't have come at a worse time.
He continued, "I am not lying - the second I sat down, the In Memoriam segment stars up... I'm smiling ear-to-ear from the best compliment of my life, and the sad music starts and we start cherishing the folks we've lost.
"It was nearly impossible for me to not smile. And Kristen was like, 'Okay, get it together.' I never got it together! We left... there's photos of me leaving an hour later, like, still smiling."