James Fisher, Everett Collection

As a wee lad, actor-comedian BILLY CRYSTAL enjoyed bedtime lullabies from his occasional baby-sitter, legendary chanteuse Billie Holiday. (Crystal’s father worked with Holiday in the music industry.) With such an indelible childhood, it’s perhaps no wonder Crystal — star of this month’s Parental Guidance, a real-life father of two and a grandfather — has devoted so much of his career to child’s play. Here, we remember some of his most childish moments on screen.

City Slickers [top] (1991)
On a “mancation,” Crystal expresses a sweet patriarchal side in the Wild West — by delivering a calf with his bare hands.
James Fisher; Everett Collection

Fathers’ Day (1997)
Crystal and Robin Williams play mid-lifers who are (un)pleasantly surprised when an ex-flame says one of them sired her adolescent spawn.

Monsters, Inc. (2001)
As neurotic one-eyed monster Mike Wazowski, Crystal, along with best bud Sulley (John Goodman), befriends a lost little girl, Boo.

Tooth Fairy (2010)
Crystal plays mystical guru to a long line of tooth-for-cash fairies, including Dwayne “The Rock” Johnson.

Parental Guidance (2012)
Having (poorly) raised a now-grown daughter (Marisa Tomei), Crystal finds himself having to cross generational divides as a curmudgeonly grandfather to three 21st-century squirts.