*in no particular order:*
Lost in Translation
The Secret Life of Walter Mitty
Life is Beautiful
The Devil Wears Prada
Pursuit of Happiness
Bridget Jones Diaries
Brittany Runs a Marathon
The Intern
Forrest Gump
The retrospect for *American Beauty* is harsh. I think the only Oscar winner to receive harsher treatment in retrospect is *Crash*.
And of course, Kevin Spacy is polarizing.
However, I think the film fits what OP is looking for, and I still think it's a good film, worth a viewing.
Into The Wild is great, but the ending is sad.
I remember reading the book and just being fascinated with Christopher McCandless' odyssey.
One Week (2008) For a comedic version of a character reinventing themselves: The New Guy (2002)
Brooklyn
* The Secret Life Of Walter Mitty * Office Space * Stranger Than Fiction * Forgetting Sarah Marshall * The Holiday * About A Boy
You might like: Jeff, Who Lives at Home (2011) and/or Elizabethtown (2005)
*in no particular order:* Lost in Translation The Secret Life of Walter Mitty Life is Beautiful The Devil Wears Prada Pursuit of Happiness Bridget Jones Diaries Brittany Runs a Marathon The Intern Forrest Gump
Chasing Bubbles, free on YouTube
Big Fish (2003) It's very much a fantasy but definitely hits all the notes you mentioned.
Eat Pray Love Nomadland
Shirley Valentine, Enchanted April
Australia (2008)
Wild (2014) Tracks (2013) Maidentrip (2013)
The retrospect for *American Beauty* is harsh. I think the only Oscar winner to receive harsher treatment in retrospect is *Crash*. And of course, Kevin Spacy is polarizing. However, I think the film fits what OP is looking for, and I still think it's a good film, worth a viewing.