Double Trouble

Don Draper and Jay Gatsby: Two Men With a Parallel and Lurid Past

Jean Trinh notes the similarities between Don Draper of ‘Mad Men’ and Jay Gatsby of ‘The Great Gatsby.’

Warner Bros. Pictures; Michael Yarish/AMC

Handsome, charismatic, enigmatic, and aloof. Are we talking about Mad Men’s Don Draper or Jay Gatsby of The Great Gatsby? Both!

The two mysterious American characters that have made an indelible mark on TV, film, and literature, are now hitting the entertainment world at the same time. Baz Lurhmann’s sparkling rendition of The Great Gatsby is out in theaters on May 10, and AMC’s Mad Men is in the midst of unveiling some juicy new surprises in its sixth season.

Both Draper (Jon Hamm) and Gatsby (Leonardo DiCaprio) have drama written all over their lives—akin to a Shakespearean play, holding similarities from the company they keep to their secretive and reinvented lives. The following is a list of ways these two dapperly-dressed and complicated men resemble one another. WARNING: Major spoilers ahead.

What’s in a Name?

Gatsby and Draper are both introduced as characters with pasts so surprising that they take great pains to keep them secret. It’s revealed that Gatsby was once a James Gatz and Draper was born to the name Richard “Dick” Whitman.


From Draper’s 1960s mod suits to Gatsby’s roaring 1920s style, it’s hard to imagine the two had roots in rural Midwestern towns. It’s uncovered in Mad Men that Draper was born in Illinois, as the illegitimate son of a farmer and a 22-year-old prostitute, who died during childbirth. Gatsby also rose from an impoverished childhood—born on a farm in rural North Dakota—with a disdain for poverty and a longing for the glitz and glamour of the wealthy.

Moving On Up

The reinvented Gatsby moved into a flashy mansion in the fictional West Egg village of Long Island, NY, to impress love-interest, Daisy Buchanan (Carey Mulligan). He used the new digs to throw some lavish ragers. In his new life, Draper lived with his family in a Westchester County, NY home—which Kapitall Wire estimates is worth $363,000 today, and worked as an ad copywriter in the heart of bustling Manhattan.

Alma Mater

Both men have dabbled in higher education. Although Draper never finished high school in his previous life, his new assumed identity led him to become a fur coat salesman by day and City College of New York student by night. Gatsby, on the other hand, attempted to attend St. Olaf’s College in Minnesota, but dropped out after two weeks because he loathed the janitorial work he had to do to pay the tuition. He had another educational stint at Oxford College in England, but it was also short-lived.

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When Draper ditched his high school efforts, he ran away to enlist in the Army for the Korean War—a move that would forever change his life and form his new identity. Gatsby met Daisy as a military officer in Louisville, KY before heading out to Europe to fight in World War I, a move that put his relationship with Daisy on hold.

New Beginnings

Draper assisted his Lieutenant, the real Donald Draper, in building a field hospital during the Korean War. However, after an explosion, the real Draper was burned to death and Whitman swapped their dog tags, assuming Draper’s identity, and even receiving a Purple Heart when he awoke in a hospital. After Gatsby returned from the war, he got involved with illegal crimes in bootlegging, a move that helped him accumulate most of his wealth.

The Love Interests

Daisy and Betty Draper (January Jones) are women you’d love to hate…and the women that Gatsby and Draper loved. Both ladies share commonalities in their beauty—Betty was a model when she met Draper, and Daisy was the aristocratic head-turner. However, they also resemble each other in their flawed childish and selfish ways. Betty is an ice queen, and fans of Mad Men remember her slapping her daughter Sally Draper (Kiernan Shipka) for cutting her hair and busting out a shotgun to kill some chirping birds. Despite Gatsby’s efforts to win Daisy’s love, she doesn’t choose him in the end and lets him take the blame for her accidental vehicular manslaughter of Myrtle Wilson (Isla Fisher). To make matters worse, she doesn’t even attend Gatsby’s funeral.

Pimp My Ride

Gatsby’s yellow Rolls-Royce is a symbol of his wealth; guests fawned over the classy vehicle at his parties. However, it played a role in his demise as Daisy accidentally ran over Wilson with the same car, eventually leading to Gatsby's murder because he was blamed for her death. Draper purchased a cool blue 1962 Cadillac Coupe de Ville when he became a partner at Sterling Cooper. He was pushed by his boss Roger Sterling (John Slattery) to buy the car, and told him having the car meant he had “arrived.”