Harry and Tonto
(I consider old 65+)
Grumpy Old Men
Grumpier Old Men
Animated:
Up
Monsieur Verdoux.
Never Give a Sucker an Even Break
Oh, God!
How about Ruth Gordon in* Harold and Maude*?
Oh God!
The Kominsky Method, with Alan Arkin and Michael Douglas as the leads.
Oh, and any Woody Allen movie… Allen Stewart Konigsberg has been playing That Old Jewish Guy for decades, kvetching like he’s Jackie Mason’s grandfather.
Woody Allen turned 65 on December 1, 2000. So any film before then doesn’t qualify. Here are Allen’s films released since then:
Company Man (2000)
Small Time Crooks (2000)
Picking Up the Pieces (2000) (actor only)
The Curse of the Jade Scorpion (2001)
Stanley Kubrick: A Life in Pictures (2001) (documentary) (himself)
Hollywood Ending (2002)
Anything Else (2003)
Melinda and Melinda (2004)
Match Point (2005)
Scoop (2006)
Cassandra’s Dream (2007)
Vicky Cristina Barcelona (2008)
Whatever Works (2009)
You Will Meet a Tall Dark Stranger (2010)
Midnight in Paris (2011)
Paris Manhattan (2012) (actor only)
To Rome with Love (2012)
Fading Gigolo (2013) (actor only)
Blue Jasmine (2013)
Magic in the Moonlight (2014)
Irrational Man (2015)
Café Society (2016)
Wonder Wheel (2017)
A Rainy Day in New York (TBC)
Stanley Kubrick: A Life in Pictures is a documentary and certainly doesn’t count. A lot of the other films listed don’t count either because he didn’t act in them himself. Even among the remaining ones, many don’t count because he didn’t play the lead role. Many of these films aren’t comedies. So only a few of Allen’s films fit the description in the OP.
In Murphy’s Romance, James Garner’s character was 60.
Well, in A Christmas Story, Darren McGavin is always referred to as “the old man.”
Leslie Nielsen was 64 when* The Naked Gun 2½: The Smell of Fear* was released and 67 when Naked Gun 33⅓: The Final Insult was released. He made more spoof comedies right up until died he died at the age of 84. IMHO, they mostly are not that great though.
Nobody’s Fool (1994), which starred Paul Newman (who was in his early 70s at the time) as well as Jessica Tandy (who was in her 80s).
Cary Grant in Father Goose.
Peter O’Toole in My Favorite Year.
Gregory Peck in Roman Holiday.
Michael Douglas, Morgan Freeman, Robert De Niro and Kevin Kline in Last Vegas. The female lead (Mary Steenburgen) was 60 when it was filmed. All 5 are Oscar winners.
Bing Crosby and Frank Sinatra in High Society.
William Holden and Humphrey Bogart in Sabrina.
Walter Matthau and Jack Lemmon in Buddy***, Buddy***.
How old was Michael Caine in Dirty Rotten Scoundrels?
Gregory Peck was 37 when he made Roman Holiday.
Yeah, but how old was Audrey Hepburn? :dubious:
All of the actors I listed were “older men” compared to their leading ladies.