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Oh, Leo. Always the Oscar nominee and never the Oscar winner. We have our fingers crossed for you this year. But just in case, we also have some literary roles that you should play that could also score you that coveted golden statue in the future.

Iago from Othello by William Shakespeare

You did the whole Romeo thing when you were a young man; this is your chance to kick it up a notch by playing a more complex role: Iago. You can turn on your classic charisma by appearing trustworthy to Othello and reveal your evil to the audience by directly speaking to them (a la Jordan Belfort in Wolf of Wall Street). When you deliver a stunning performance as Iago, we are sure all the competition will be green-eyed with envy.

 

Lord Henry from The Picture of Dorian Gray by Oscar Wilde

Our first impulse would be to cast you as Dorian Gray, we are sure you would do a smashing job of it, but we are afraid you are too old for the part (alas, there are no magic pictures in real life; Photoshop will only go so far). Time is cruel, we know. Still, we think you would be fabulous as Lord Henry. We believe you could easily make the hedonistic life seductive, and we are sure your corruption of Dorian would be appropriately horrifying and enthralling. While you would not win Best Actor, we definitely think you would get Best Supporting Actor.
 

John Dowell from The Good Soldier by Ford Maddox Ford

Critics and judges seem to love unreliable narrators, so we think the role of John Dowell is Oscar bait. Besides get rave reviews from critics, we are sure the fragmented and non-chronological narrative will force audiences to see the film more than once, generating more revenue.

 

Rabbit from The Rabbit Teratology by John Updike

After seeing you in Revolutionary Road, we realized that you play suburban angst really well. This would be your chance to do it again, but over four different decades. Not only would you get a chance to try different fashion and hairstyles, but you would also get to enact different stages of life. To top it all off, it would require four films (potentially five if you want to split the last film in two), so you are quadrupling your chance of winning an Oscar.

 

Sherman McCoy from The Bonfire of the Vanities by Tom Wolfe

We know you can play a wealthy man on Wall Street based on your performance in The Wolf of Wall Street. We also are aware that you have played a character who was involved in a hit and run in The Great Gatsby. You can combine the two elements as Sherman “Master of The Universe” McCoy in The Bonfire of the Vanities. Since the two individual roles didn’t seem to do the trick for the Academy, maybe combining elements of the two will finally get you the award.


Sarah Fox's picture

Sarah Fox

Sarah Fox is an editor, writer, writing consultant, and pop culture enthusiast. Besides regularly contributing to Quirk Books’ blog, she has published an edition of William Shakespeare's Measure for Measure. She lives in Washington D.C. with her husband and Pembroke Welsh Corgi. You can find her online at www.thebookishfox.com.