Christopher Plummer – 88
You may remember him from the movies such as ‘The Sound of Music’, ‘Waterloo’, and ‘The Insiders’, but his eponymous performance came in the 1952 movie ‘Sage Struck’. Plummer only won his Academy Award when he was 82! Across 6 decades, he built up a net worth of $20 million. He would surely be able to spend his retirement in peace and without fiscal worries.