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Best & Worst Older/Younger Character Portrayal

Joseph Gordon-Levitt did a pretty good job as a younger Bruce Willis in Looper, IMHO. But I’m still pretty glad they never did the proposed 6th Die Hard film that would’ve supposedly featured a young, pre-Nakatomi Plaza McClane and also Bruno in a modern setting.
 
Ditto. He didn't have the right energy or cadence. And frankly, Alden Ehrenreich has an *enormous* head, so it would be hard to pass him off as...well...anyone else.
The Face of Boe?

Others who spring to mind - the younger and older princesses in House of the Dragon were very well cast IMHO. Also, Robert Aramayo as a younger Ned Stark in Game of Thrones did pretty well as a younger Sean Bean
 
Mckenna Grace probably needs to be mentioned. She was young Margot Robbie in I, Tonya, young Brie Larson in Captain Marvel, and young Kiernan Shipka in Sabrina the Teenage Witch, among others.
 
young Margot Robbie
young Brie Larson
young Kiernan Shipka
Continuing the trend, Grace also has a recurring role on Young Sheldon. But that's not quite the same thing. ;)

Now that I mention it, though, Iain Armitage does quite a nice job on that show as the young Sheldon Cooper.
 
While looking nothing alike, Dominic Cooper and John Slattery do a good job portraying young and old Howard Stark.
 
Continuing the trend, Grace also has a recurring role on Young Sheldon. But that's not quite the same thing. ;)

Now that I mention it, though, Iain Armitage does quite a nice job on that show as the young Sheldon Cooper.

Zoe Perry really looks like her mother Laurie Metcalf, so that helps in her portrayal of Sheldon's mom.
 
Continuing the trend, Grace also has a recurring role on Young Sheldon. But that's not quite the same thing. ;)

Now that I mention it, though, Iain Armitage does quite a nice job on that show as the young Sheldon Cooper.
So which of the three should play "Old" Paige?
Speaking of Young Sheldon/BBT. Montana Jordan and Jerry O'Connell are a good match as young/old Georgie Cooper. Sheldon's mom is a bit of a cheat as she is played by a mother/daughter combo: Laurie Metcalf/Zoe Perry
 
Alden Ehrenreich as a young Han Solo just didn't work for me.
Me, either - a horrible casting decision. By contrast, I love how well Ewan McGregor channeled Alec Guinness for the prequels. He studied many of his various performances like crazy, trying to nail his mannerisms down. Hayden Christensen had more freedom, since Anakin was pretty much a blank slate as a young man.
 
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