Roger Sterling is a US Navy veteran of World War II, having served in the Pacific theater, including in the Battle of Okinawa.

Sterling is a notorious womanizer and a heavy smoker and drinker (living like he was "on shore leave") until two heart attacks in the same year force him to slow down, at least for a while.

Numerous episodes in the third season imply that he is genuinely happy with Jane: for example, he turns down an old flame trying to rekindle their relationship.

She marries a very suitable young man, Brooks Hargrove (Derek Ray), of the same class and social set into which she was raised.

Roger and Mona effectively disown Margaret, and help to raise their grandson, and are shown to be watching the Apollo Moon landing with him.

The series periodically explores the romantic tension between Roger and his former mistress, Joan Holloway (Christina Hendricks).

Roger, however, secretly makes deals to keep Don, arguably out of remorse for similar behavior that cost the firm an account with Honda, in his case launching into an anti-Japanese tirade.

When Don marries his secretary Megan Calvet (Jessica Paré), Roger meets her mother Marie (Julia Ormond), and the two have a brief but intense affair.

He has also won the Screen Actors Guild Award for Outstanding Performance by an Ensemble in a Drama Series twice along with the cast of Mad Men.