So there's several high caliber films I've seen a bunch, like Pulp Fiction, Memento, etc.. but I think the actual movie I've seen the most times is The Room.
For the uninitiated, The Room is the worst movie of all time. Tommy Wiseau wrote, produced, directed, and starred in this disasterpiece. It's so bad, they made a movie about the book about the making of The Room. It's like watching a train wreck in slow motion for 90 minutes.
I've been responsible for many people's first viewings, which means I've seen it far, far more than I should. I almost got to meet Tommy and Greg (plays Tommy's best friend in film) at a screening but icy ass rain made the trek too dangerous.
I'd say it's a must see for anyone who enjoys film. Every other movie will feel better after comparing it to this flaming bag of garbage. You'll laugh, you'll cry, and you'll say "wtf" at least 7 times.