The Holdovers (2023) – Paul Giamatti as "Mr. Hunham"

The Angel of Rome (2022) – short story by Jess Walter

Ovid and the Art of Love (2019) – film by Esme Von Hoffman

The Confessions of Frances Godwin (2014) – novel by Robert Hellenga

Regular Show: Season Five, Episode 22 (2014) – David Kaye as "Latin Teacher"

The Mindy Project: Season One, Episode 13 (2013) – B.J. Novak as "Jamie"

Ready Player One (2011) – novel by Ernest Cline

An Education (2009) – Kate Duchene as "Latin Teacher"

Leaves of Grass (2009) – Edward Norton as "Professor Kincaid"

Love Comes to the Executioner (2006) – Jonathan Tucker as "Mr. Prigusivac"

The Ladykillers (2004) – Tom Hanks as "Professor Dorr"

The Lake of Dead Languages (2002) – novel by Carol Goodman

The Emperor's Club (2002) – Kevin Kline as "Mr. Hundert"

Goodbye, Mr. Chips (2002) – Martin Clunes as "Mr. Chipping"

Where Did Miss Nancy Sterett Go? (2002) – song by David Massengill

The Last Dance (2000) – Maureen O'Hara as "Ms. Parker"

Forum Romanum: Episode 22 (1999) – Ken Kitchell as "Magister"

The Fall of a Sparrow (1998) – novel by Robert Hellenga

A Feast at Midnight (1994) – Christopher Lee as "Major Longfellow"

The Browning Version (1994) – Albert Finney as "Mr. Crocker-Harris"

The Man Without a Face (1993) – Mel Gibson as "Mr. McLeod"

The Secret History (1992) – novel by Donna Tartt

Class Act (1992) – Rhea Perlman as "Ms. Simpson"

Dead Poets Society (1989) – Leon Pownall as "Mr. McAllister"

Goodbye, Mr. Chips (1969) – Peter O'Toole as "Mr. Chipping"

"So Much Unfairness of Things" (1962) – short story by C.D.B. Bryan

Personal Affair (1953) – Leo Genn as "Mr. Barlow"

The Browning Version (1951) – Michael Redgrave as "Mr. Crocker-Harris"

The Happy Years (1950) – Leo G. Carroll as "The Old Roman"

Hets (1944) – Stig Jarrel as "Caligula" 

Goodbye, Mr. Chips (1939) – Robert Donat as "Mr. Chipping"

Goodbye, Mr. Chips (1934) – novella by James Hilton

Holiday Romance (1868) – novella by Charles Dickens

Know of others? Please let me know.