Suggestions by @milanthaitlach506946

Bonnie Hunt

as Female Shaw in Open Season (Gender Swap)

George C. Scott

as Mayor Shellborne in Cloudy with a Chance of Meatballs (1980's)

Samuel E. Wright

as Earl Deveraux in Cloudy with a Chance of Meatballs (1980's)

Albert Finney

as Manny in Cloudy with a Chance of Meatballs (1980's)

Christopher Lloyd

as Tim Lockwood in Cloudy with a Chance of Meatballs (1980's)

Cheech Marin

as Brent in Cloudy with a Chance of Meatballs (1980's)

Jim Varney

as Steve in Cloudy with a Chance of Meatballs (1980's)

Joan Cusack

as Sam Sparks in Cloudy with a Chance of Meatballs (1980's)

Matthew Broderick

as Flint Lockwood in Cloudy with a Chance of Meatballs (1980's)