Not really a retirement movie but Takeshi Kitano's film "Kids return" is kinda related. It's about two young guys and some of their highschool classmates each taking a different path in life. The main two characters go for professional boxing and the other goes for the gangster career. The other supporting characters go for various jobs, from stand up comedy to taxi driving.
It's a really good movie with the right ballance between funny and serious and its ending has a very positive message to give to the audience.

Then there's Akira Kurosawa's "Ikiru" about a dude who works at the city hall and finds out he's ill and dying so he makes it his single goal to overcome the burecracy and manage to make the city remake a nasty garbage drain or some such into a playground for kids, a request of the local people that has been rejected everytime they submitted it through his office before.