Leonardo DiCaprio and Timothy Olyphant in Once Upon a Time... in Hollywood (2019)

Conan O'Brien and Timothy Olyphant in Timothy Olyphant (2019)

Timothy Olyphant in Timothy Olyphant (2019)

Drew Barrymore and Timothy Olyphant in Santa Clarita Diet (2017)

Timothy Olyphant in Santa Clarita Diet (2017)

Brad Dourif, Powers Boothe, Paula Malcomson, Ian McShane, Timothy Olyphant, Molly Parker, and Robin Weigert in Deadwood (2004)

Conan O'Brien and Timothy Olyphant in Conan (2010)

Timothy Olyphant and Jeff Ross in Conan (2010)

Timothy Olyphant and Liv Hewson in Santa Clarita Diet (2017)

Drew Barrymore, Timothy Olyphant, and Liv Hewson in Santa Clarita Diet (2017)

Maggie Lawson, Joel McHale, and Timothy Olyphant in Santa Clarita Diet (2017)

Gerald McRaney and Timothy Olyphant in Santa Clarita Diet (2017)

Pedro Pascal and Timothy Olyphant in The Mandalorian (2019)

Timothy Olyphant in The Mandalorian (2019)

Timothy Olyphant in Justified: City Primeval (2023)

Conan O'Brien and Timothy Olyphant in Timothy Olyphant (2020)

Timothy Olyphant in Timothy Olyphant (2020)

Glenn Close, Dermot Mulroney, Joshua Jackson, Mary Kay Place, Patricia Clarkson, Moira Kelly, and Timothy Olyphant in The Safety of Objects (2001)

Sarah Polley, Katie Holmes, and Timothy Olyphant in Go (1999)

Powers Boothe, Keith Carradine, Ian McShane, Timothy Olyphant, and Molly Parker in Deadwood (2004)

Paula Malcomson, Ian McShane, Timothy Olyphant, and Molly Parker in Deadwood (2004)

Juliette Lewis, Kevin Smith, Jennifer Garner, Sam Jaeger, Timothy Olyphant, and Joshua Friesen in Catch and Release (2006)