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You are able to buy "My Generation" on Apple TV as download.
There are no options to watch My Generation for free online today in Canada. You can select 'Free' and hit the notification bell to be notified when show is available to watch for free on streaming services and TV.
A documentary crew follows the stories of nine classmates during their high school years in Austin, Texas, and then revisits them ten years later to examine how far they have come.