- Held dual American-Canadian citizenship.
- Rakoff worked in book publishing after studying at Columbia University, and made his name crafting incisive essays for The New York Times Magazine and other acclaimed publications.
- Rakoff's popular works include his essay collection 'Fraud' and 'Half Empty', a defense of pessimism for which he earned the Thurber Prize for American Humor.
- In addition to his work in the theater and occasional roles on television, Rakoff appeared in and adapted the screenplay for The New Tenants (2009), a film that won the Academy Award for best live action short in 2010.
- Rakoff adapted the screenplay for the Academy Award-winning short film The New Tenants (2009) originally written by Anders Thomas Jensen.
- Friend and colleague of David Sedaris.
- His work, "Half Empty," was awarded the Thurber Prize for American Humor.
- Rakoff attended high school at the Forest Hill Collegiate Institute, graduating in 1982. In the same year he moved to New York City to attend Columbia University, where he majored in East Asian Studies and studied dance.
- Rakoff spent his third year of college at the School of Oriental and African Studies in London and graduated in 1986.
- Rakoff worked in Japan as a translator with a fine arts publisher.
- His work was interrupted after four months when, at age 22, he became ill with Hodgkin's disease. He returned to Toronto for 18 months of treatment, including chemotherapy, radiation, and surgery.
- From 1982, Rakoff lived in the United States, first as a student, then as a resident alien. In the early 1990s he was issued a green card, a subject he wrote about in one of his early newspaper articles.
- Rakoff chronicled the experience of becoming an American citizen in an essay published in Don't Get Too Comfortable. He became a U.S. citizen in 2003 as well as retaining his Canadian citizenship.
- In 2010, while writing the book 'Half Empty', Rakoff was diagnosed with a malignant tumor and began chemotherapy.
- Rakoff was a prolific freelance writer and a regular contributor to Conde Nast Traveler, GQ, Outside Magazine and The New York Times Magazine. His writing has also appeared in Business 2.0, Details, Harper's Bazaar, Nerve, New York Magazine, Salon, Seed, Slate, Spin, The New York Observer, Vogue, Wired and other publications.
- Rakoff appeared as himself in the documentary "Florent: Queen of the Meat Market" (2009) about a local restaurant and in a film about the book "State by State" (2008), in which one of his essays is published.
- Raised in Toronto.
- He is survived by his brother, Simon Rakoff, a comic in Toronto, Ontario, Canada; and a a sister, Ruth Rakoff, a cancer survivor and author.
- He was raised in Toronto, Ontario, Canada. He earned a Bachelor's Degree in East Asian Studies from Columbia University in 1986 in New York City. He lived as a translator in Japan until he was diagnosed with cancer. He returned to Canada and remained there until the early 1990s.
- He returned to New York City and became a social anthropologist of post modern life, author, and essayist.
- His works, 'Fraud' and 'Don't Get Too Comfortable', were awarded the Lambda Literary Awards.
- Son of Dr. Vivian Rakoff, a psychiatrist, and Dr. Gina Shochat-Rakoff, a physician of Toronto, Ontario, Canada.
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