Dated: 1986

She helps people put their lives back together for a living, he picks their labors of love apart in his reviews. She shares with her guests advice for how to move forward, he tells players in the movie industry how not to suck. Their pairing was the not-so-classic match between the generous supporter and the cutting critic.

Had they lasted beyond two dates, Oprah and Ebert could have joined forces to create a gladiator-style show where authors and directors would compete for their highly desirable stamp of approval.