9. Gigli (2003)
This film has landed near the top of virtually every worst movie list ever made, but there's still no consensus about the pronunciation of the title. Supposedly you find out if you watch the entire career-killing movie, but you'll see a Criterion edition of Gigli before the Complex Pop Culture team takes the time to sit through this atrocity.
That guarantee goes out the window if Drake or Kendrick Lamar references Gigli in song anytime soon, and we're called upon to write the "Top 25 Hip-Hop References to Awful Movies, and What They're Really Saying" list. That just comes with the territory.