"Guess the movie from the Screenshot" game

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Claire’s gone back in time! No clue.
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Actually, yup, it is.

In that third pic you have grabbed one of the scenes of the filming of Glen or Glenda recreated in Tim Burton's Ed Wood. That is Johnny Depp as Ed Wood as Glenda.
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Looks like Mickey Mantle on the right in the middle shot and Steven Hill in the bottom shot, which possibly makes this It's My Turn?
Yup, it's It's My Turn (1980).

The first pic in that first trio is Daniel Stern, post-Breaking Away/pre-Diner. Michael Douglas plays a former Major Leaguer who retired early due to injury and in one scene he takes part in an Old Timers Day at Yankee Stadium with real MLB legends, including Roger Maris and Mickey Mantle. The film also features Charles Grodin and an early appearance by Dianne Wiest.