Danny DeVito plays John Leary, a widowed father trying to raise his two sons amidst personal and societal turmoil.
Gary Sinise portrays Norman Strick, a neighbor who becomes a source of support for the Leary family.
Julia Louis-Dreyfus takes on the role of Peggy Etinger, a friend who offers companionship to John Leary.
Reese Witherspoon plays Karen Morris, a teenage girl who forms a bond with Jack Leary.
Robert J. Steinmiller Jr. portrays Jack Leary, a young boy navigating the challenges of growing up without his mother.
Miko Hughes plays Dylan Leary, the younger son of John Leary who copes with the loss of his mother.
Art LaFleur portrays Mr. Festinger, a character involved in the lives of the Leary family.
Stefan Gierasch plays the role of Father-in-Law in the film.
Erica Yohn takes on the role of Mother-in-Law in the storyline of Jack the Bear.
Andrea Marcovicci portrays Elizabeth Leary, the deceased wife of John and mother of Jack and Dylan.
Bert Remsen plays the character Mitchell in the film.
Carl Gabriel Yorke portrays Gordon Layton in Jack the Bear.
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