Rakoff was a longtime contributor to the radio show "This American Life" and the author of three books: "Fraud," "Don't Get Too Comfortable" and "Half Empty." Published in 2010, "Half Empty" won Rakoff the 2011 James Thurber Prize for American Humor.
Rakoff, a native Canadian, made his home in New York. He traveled for his writing and, in "Half Empty," wrote about visiting Hollywood. Here's an excerpt:
"When I first got here, I found the breadth of the names of those enshrined in the Walk of Fame unutterably depressing, with its embarrassment of people who are all but unrecognizable. Every step was a cruel reminder of the heartlessness of time and tide. For every Heddy Lamarr to make you recall what a brilliant, patent-holding beauty she was, there is a Barbara La Marr to keep you cognizant that someday you, too, will be dead and the subject of a great, cosmic shrugging 'Who?'... But as the days pass and I spend more and more time with the pavement, I revise my opinion."