Goodbye Mr. Chips (Herbert Ross, 1969)
Role: Gentle schoolmaster Arthur Chipping
From the novel by James Hilton, this version of Goodbye Mr. Chips is updated as a musical, but it's better not to think of it that way. The music and lyrics are not particularly thrilling and O'Toole's voice is nothing to write home about. The film is better viewed for what I think it truly is, a gentle, sentimental tale about a shy schoolmaster who falls in love with an outre music hall singer (Petula Clark). As cliche as that premise sounds, the movie works because of the chemistry between the leads. Chips is O'Toole's most nuanced, subdued performance on this list, possibly in his whole career. That he succeeds in that role as much as any bombastic king or madmen is an achievement and an intriguing thought. I wish O'Toole had taken the gentler turn more often.
The film itself was not a box office success and it's easy to see why. It sort of defies categorization. Like I said, it fails to impress as a musical, especially when compared to its compatriot and 1968 Best Picture winner Oliver! It's a period piece, spanning the 1920s-present day (late 1960s) in English history. In every period, Chips is out of place. His conservatism is mocked by the Lost Generation, he can't understand why the school is under siege during the air raids of WWII, and after his wife dies, he is as lost as ever, retreating to the memories of happier days. Chips is a man out of time, only content when he and Clark have married. She slower starts to open up Chips' world, becoming the beloved "mother" of all the students, past and present, at the all boys school.
This clip demonstrates the gentle sentimentality and fond nostalgia that infuses the entire film as O'Toole, after a lecture where he's failed to connect to his students, reminisces about his own bygone school days: