Wizard of Odds: Who Will Play Dorothy in the Wizard of Oz Remake?

Yet another Wizard of Oz remake is in the works again, with Watchmen director Nicole Kassel slated to direct an adaptation of L. Frank Baum’s novel in a remake for New Line Cinema. The film has been remade several times, although the 1939 musical starring Judy Garland is the most recognizable, iconic, and classic version.

While the latest remakes like the Oz the Great and Powerful starring Mila Kunis and James Franco and the Muppets’ Wizard of Oz haven’t necessarily held the same pomp, splendor, and distinction of the 1939 version (which isn’t the first adaptation of the novel), Kassel’s moody & atmospheric directing style could take this remake in an entirely new, albeit welcome, direction. With so many different types of Wizard of Oz remakes, this version could pay homage to the classic heavily, or faintly — with that in mind, who’s most likely to be off to see the wonderful Wizard of Oz? Let’s look at the favorites, the underdogs and considerations for each role.

Wizard of Oz Odds: Who will star in the remake?

So, who will fill the ruby red slippers big shoes left behind by the ’39 version of Wizard of Oz? Here’s a preview of the latest odds for favorites (and underdogs) to star in the upcoming movie via Bovada.

Who will play Dorothy in the Wizard of Oz remake?  

The favorite to play Dorothy is Stranger Things’ star Sadie Sink. The actress is slated to star in another film adaption, the slightly different Fear Street, and will have a role in Dear Zoe, which is currently in post-production.

Will age play a factor? The featured actresses birthdays range from 1992-2002, with the underdog, Miley Cyrus born in, and the favorite, Sadie Sink born in ’02. It’s unclear if this remake will be a musical, but singing skills will definitely come in to play — while Sadie Sink isn’t known for singing professionally she definitely has some vocal chops, and it’s unclear is Nacon has singing skills that rival Grande or Cyrus. Speaking of Grande — the ‘7 rings’ singer won a National Youth Theatre Association Award for her role as Charlotte in the musical 13, and was also a standout as Penny Pingleton in the most recent live action stage adaptation of Hairspray. If it is in fact a remake, we expect the line movement to creep up in Grande’s favor.

The main question on our mind is — will Dorothy become a redhead? Only time will tell.

Performer Odds
Sadie Sink +140
Hailee Steinfeld +160
Katelyn Nacon +225
Ariana Grande +600
Miley Cyrus +600

Ariana Grande during the “Hairspray Live!” Press Junket in 2016.

Who will play the Cowardly Lion in the Wizard of Oz remake?

When you think of a coward, do you think of Dwayne ‘The Rock’ Johnson? Maybe not, but we can certainly see him as the hunkering, cowardly, and apprehensive lion. Johnson’s size would definitely create an interesting juxtaposition as the jittery lion. The favorite is Jon Bernthal, who’s career is definitely on a hot-streak, with upcoming roles in the Sopranos prequel Many Saints of Newark, King Richard, and Those Who Wish Me Dead — a role as the Lion would be a sharp departure from his recent dramatic roles, which could help him carve out his nitch (even further) as a versatile actor.

Can underdog Bautista make yet another move from the wrestling ring to the action screen, to the yellow brick road? Perhaps — Dave Bautista is the underdog at +600 to be cast as the cowardly lion, which would make the role as the lion a big shift for him. Just like favorite Jon Bernthal.

Performer Odds
Jon Bernthal +140
Dwayne ‘The Rock’ Johnson +160
Jack Black +225
Andy Serkis +600
Dave Bautista +600
cowardly lion costume on display at museum

Bert Lahr’s original Cowardly Lion costume.

Who will play the Scarecrow in the Wizard of Oz remake?  

David Tennant is the favorite only slightly ahead of Lin-Manuel Miranda, who has more than proved he has the chops to join a standout cast in a critically-acclaimed musical.

Shia Labeouf is the underdog to be cast as the Scarecrow, and this looks even less likely to happen as Labeouf’s management agency, CAA dropped him at the time of writing.

Performer Odds
David Tennant +140
Lin-Manuel Miranda +160
Ryan Gosling +225
Brad Pitt +600
Shia Labeouf +600

Who will play the Tinman in the Wizard of Oz remake?

Neil Patrick Harris has already proved that his family makes a picture-perfect remake of the Wizard of Oz cast — will Harris himself be the next Tinman? While he’s the frontrunner to take the role of the tender-hearted heartless tin man, Timothee Chalamet certainly stunned in a recent commercial as ‘Edgar’ Scissorhands, and definitely has the ability to fill the roles’ (tin) shoes.

Performer Odds
Neil Patrick Harris +140
Robin Lord Taylor +160
Jackson Harper +225
Kit Harrington +600
Timothee Chalamet +600

Who will play the Wicked Witch in the Wizard of Oz remake?

Elizabeth Banks is the favorite to play the Wicked Witch — there’s no doubt her role as Effie Trinket, the eccentric Hunger Games announcer contributes to her lead. Angelina Jolie, the underdog, has experience embodying a classic cartoon villain as her role as Maleficent proves, although we think it’s unlikely she’d be typecast in another iconic villain role.

On a personal note, we think it’s unlikely that Jolie would be cast at the Witch and Pitt, her ex-husband as the Scarecrow — can you imagine the press tour?

Performer Odds
Elizabeth Banks +140
Meryl Streep +160
Lena Headey +225
Angelina Jolie +600
Tessa Thompson +600

Who will play the Wizard of Oz in the Wizard of Oz remake?

Mark Hamill is the favorite to play the Wiz – we think this could largely be because of the likeness he shares with the original Wiz, Frank Morgan (who also plays the Gatekeeper, Professor Marvel, the Carriage Driver and the Guard).


Ian McKellan, who’s also favored to play the Wiz, certainly evokes a more ‘wizard-like’ look and feel than Hammill, and his turn as Gandalf in the Lord of the Rings film series helps. Did you know that McKellan was tapped to play another iconic, fictional wizard? McKellan was approached to play Dumbledore in the Harry Potter series after the original actor, Richard Harris passed, but turned it down because Harris didn’t like him — McKellan felt it was wrong to take the part on from an actor who didn’t respect him.

Steve Martin feels less likely to embody a wizard, although we can definitely see him as the man behind the curtain. Plus, if this version of the film is a musical, his musical abilities will lend themselves well to the role.

Performer Odds
Mark Hammill +140
Ian McKellan +160
Tom Hanks +225
Patrick Stewart +600
Steve Martin +600

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