What actor/actress was in these movies?

Actually it was the shot of McDormand I remembered from This Must Be the Place

Reign Over Me + Cowboy Up* + Staying Together + Magnolia =
Melinda Dillon



*another Googling error: posted a still from the wrong Cowboy Up



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Haven’t a clue

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Old

Empty Holsters + Fort Apache + Please Murder Me! =
Dick Foran



But the fourth movie, The Four Skulls of Jonathan Drake, doesn't fit so I don't know if that's what @Gideon58 was looking for?

Dick Foran is what I was looking for, you're up, Holden

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Beverly Hills Chihuahua + Desperado + The Cannonball Run II =
Cheech Marin



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Can't tell what the middle one is but Wild Orchid 2:Two Shades of Blue + Black Moon (1975) =
Joe Dallesandro






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No clue

Top shot looks like Me Earl and the Dying Girl?

Me and Earl and the Dying Girl + Ready Player One + Thoroughbreds =
Olivia Cooke

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Ten different films, one common performer...

OK, I've got Richard Kind, Sean Astin, Kyra Sedgwick, America Ferrera, Jason Lee, Olivia Wilde, Dylan McDermott, Richard Gere, and Michael McKean, the Sedgewick and McDermott shots look vaguely familiar, but i can't identify any of the movies.

Those are definitely nine of the ten actors. Vinnie Jones is the other.