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People seem to have a love-hate relationship with Zach Braff’s work. But besides being an actor, the Scrubs alum is an experienced producer, director, and screenwriter who’s worked alongside Natalie Portman, James Franco, Morgan Freeman, and more.

In the realm of funny Morgan Freeman stories, Braff can claim bragging rights for one involving a friendly bet with the veteran actor.

Morgan Freeman and Zach Braff
Morgan Freeman and Zach Braff at the ‘Going In Style’ New York premiere | Mike Coppola/Getty Images

Zach Braff and Morgan Freeman worked on a film together

In 2017, Going In Style was released in theaters and starred Freeman, Michael Caine, Ann-Margret, Alan Arkin, Kenan Thompson, Matt Dillon, and Christopher Lloyd. Braff directed the remake film about a threesome of buddies played by Freeman, Arkin, and Caine who stop being squares and start robbing banks after losing their pensions.

During an interview with Entertainment Weekly, Braff praised his main trio of actors as wonderful and shared that they did most of their stunts.

“They rarely said no to doing something, and I had pretty elaborate stunt sequences with them riding this stolen electric shopping cart through the streets of Williamsburg and weaving in and out of cars and firing guns,” said Braff.

Freeman was tangled up in a bet with Braff

Off camera, Braff and Freeman shed their Hollywood deal-making abilities in favor of an old-fashioned casual bet.

It was Freeman’s last shot, and he didn’t believe that Braff would be able to wrap up filming ahead of schedule. The odds were not tilted in Freeman’s favor, and as a result, he had to put his famous “Voice of God” to use.

What did he have to do? Freeman recorded the outgoing message for Braff’s voicemail, which by all accounts, is probably still active.

He told Seth Meyers that people ask him to do that all the time and he always turns the requests down. Additionally, Freeman’s voice isn’t even on his own personal phone’s voicemail. Years later, Braff is still winning.


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Freeman recently teamed up with Braff again

Braff and Freeman reunited for 2020’s The Comeback Trail, a comedy that features both actors alongside Robert De Niro, Tommy Lee Jones, Eddie Griffin, and Emile Hirsch.

According to the movie’s logline from IMDb, it’s about two producers in trouble with the mob:

In debt to the mob and in need of a new money making scheme to save his skin, greedy grind-house film producer, Max Barber, (Robert Deniro) decides to produce a dangerous new film, all for the sake of killing his lead actor in a stunt so he can rake in the insurance money. But when he casts Duke Montana, (Tommy Lee Jones) an aging, washed up movie star as the lead, Max never expects the depressed old drunk to be revitalized by being in front of the camera again. Unable to kill Duke in a basic stunt, Max ups the stakes, putting Duke into ever more dangerous situations. And as Duke survives stunt after stunt, Max unwittingly starts making the best movie of his career.

Braff plays Max’s nephew and Freeman plays Reggie Fontaine. The film had a limited release but will be available nationwide in 2020.