Cooper is not only starring but is also making his directorial debut with the film, according to The Hollywood Reporter.
The movie is based on the 1937 film starring Janet Gaynor and Fredric March.
The story centers on a movie star, who helps an aspiring young actress find fame, even as age and alcoholism send his own career into a downward spiral.
It was subsequently remade in 1954 by director George Cukor, with Judy Garland and James Mason starring, and again in 1976, with Barbra Streisand and Kris Kristofferson toplining.
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Chappelle will play a character named Noodles, who is Cooper's character's oldest friend.
Bill Gerber, Jon Peters, Todd Phillips and Lynette Howell Taylor are producing with Cooper.
Basil Iwanyk and Ravi Mehta are executive producing.
Cooper also had a hand in crafting the script, with Will Fetters and Eric Roth also writing.
The film is scheduled to release on September 28, 2018.
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