27. The Man In The Iron Mask (1998)
DiCaprio's first movie after launching to superstardom with the one-two punch of Romeo + Juliet and Titanic, The Man in the Iron Mask finds the actor pulling double duty as the eponymous prisoner and the villainous French king Louis XIV.
Compelling as this may sound on paper - not just blending DiCaprio's boyish charm with his desire to tackle more mature material, but pairing him with the likes of John Malkovich, Gabriel Byrne, and Jeremy Irons as the Three Musketeers - the film itself is a stifled mess that refuses to give its cast any time to breathe.
Stuffed with dull action and ineffective twists, The Man in the Iron Mask suffocates its stars, and DiCaprio, much stiffer and more uncertain than ever before, comes off worst, seemingly lost amongst the rubble of the adventure film's obvious potential.