Suggestions by @biopicfan

Jim Carrey

as Dr. Doofenshmirtz in Phineas and Ferb (live-action)

Joseph Gordon-Levitt

as John Wilkes Booth in Sic Semper Tyrannis

Topher Grace

as Gene Saks in Bea

Grace Gummer

as Bea Arthur in Bea

Ben Affleck

as Robert Alan Aurthur in Bea

Julianne Moore

as Alice Decker-Simmons in Parental Guidance (2002)

Jenna Ortega

as Brenda Ayres in One Night in Miami

Keke Palmer

as Sonji Roi in One Night in Miami

Adrien Brody

as Angelo Dundee in One Night in Miami

Jesse L. Martin

as Elijah Muhammad in One Night in Miami

Jennifer Hudson

as Betty X in One Night in Miami

Louis Cordice

as Louis X in One Night in Miami

Rocky Carroll

as Thomas 15X Johnson in One Night in Miami

Trevor Jackson

as Norman 3X Butler in One Night in Miami

Leon Robinson

as Talmadge Hayer in One Night in Miami

Jake Gyllenhaal

as Allen Klein in One Night in Miami

Brenda Song

as Elisa Boyer in One Night in Miami

Mo'Nique

as Bertha Franklin in One Night in Miami

Zoe Saldaña

as Barbara Campbell Cooke in One Night in Miami

Blair Underwood

as Sonny Liston in One Night in Miami