Glee Hot Seat #3
 

Continued from last thread:

Come on guys, it's not that hard.
Maybe we could do it one character at a time.
For example: Will Shuester:
1950s: Mickey Rooney
1960s: James Darren.
1970s: Sonny Bono
1980s: Tom Hanks
1990s: Jim Carrey.
Rooney could sing, dance and act so well not much would be expected from his young co-stars, but it's not hard to think of a few that could keep up. His height makes him a natural loser despite talent.
James Darren (not to be confused with Bobby Darren) could barely sing and barely act, but with Barbra Striesand as Rachel, Nancy Sinatra as Quinn and Aretha Franklin as Mercedses who would care? His boyish face would create crush episodes for every female and whoever played Kurt.
Sonny Bono in 1977 became a loser and always looked like one.
Tom Hanks would have had his talent discovered five years early.
Jim Carrey could have transitioned from zany comedy as the star in season one to a dead-serious supporting part by the last season, giving him a stronger and more diverse acting career than he really had.
There's no need for essays. Any nice daydream would be welcome!

It's just hard to think of a lot of actors from certain decades who can sing well.

I would say maybe Vera-Ellen for Quinn or Brittany.

Brittany:
1950s: Marilyn Monroe
1960s: Goldie Hawn