After Draper, the classic cool guy of the Mad Men series is certainly Roger Sterling. This silver fox has plenty of secrets to hide, and he’s the biggest flirt on the show. From a hatred for the Japanese – he’s still not over Pearl Harbor – to his overpowering love of drink and dames, this character was a breath of fresh air in a serious show thanks to his quick wit and easy charm.
This ultra-conservatively dressed character even loosens up as the show goes on, letting his sideburns grow out and adding a classic seventies mustache to his look as the show bleeds into the new decade.
Jared Harris as Lane Pryce
Jared Harris is an older name in Hollywood, having appeared in movies such as Lost in Space and Resident Evil: Afterlife. Pryce is a financial whiz who joins the main cast when Sterling Cooper is bought by a British ad agency before it turns into Sterling Cooper Draper Pryce – that's his name at the end.
At first this buttoned-up character is little more than the foreign overlord's rep, but he's made a named partner after firing the company. He's a stiff, prideful man, and his problems with the Inland Revenue (the British version of the IRS) and his refusal to ask for help lead to plenty of big problems for everyone.
Jared Harris Now
Lane Pryce dramatically commits suicide when Draper catches him embezzling from the company, and the character leaves the show in infamy. His actor, however, has gone on to appear in plenty of big productions. Since he finished on Mad Men, He's been in television shows such as The Expanse, The Crown (as King George!), The Terror, Chernobyl, Carnival Row, and even Foundation as Hari Seldon.
There have also been plenty of movies, such as Morbius, Allied, The Last Face, Certain Woman, Baby, Baby, Baby, The Man from U.N.C.L.E., and The Mortal Instruments: City of Bones. This regal actor has nothing in his way, and we're sure he'll keep popping up everywhere.
John Slattery Now
Since hanging up Sterling's suits, Slattery has been plenty busy. He's had roles on Wet Hot American Summer: First Day of Camp, The Real Mad Men of Advertising as the narrator, The Romanoffs, Modern Love, Mrs. America, Veep, and Next. He's also become a character in the Marvel Cinematic Universe as Howard Stark, Tony Stark's father, appearing in four of those films.
He also appeared in Jack & Bobby with Paré, and also voiced the ally-turned-traitor Admiral Havelock in the video game Dishonored, a series well-known for getting big names for the voices. He's also been in Ted 2, as well as a number of TV movies.
Kevin Rahm as Ted Chaough
From one of the main advertising competitors for SCDP to one of the main love interests to Peggy, Kevin Rahm shines as Chaough until season seven, which saw his role greatly reduced – he didn't even appear in the last two seasons of the show. Though opposite to Draper in almost every aspect, the two eventually develop a mutual respect.
Before the show, Rahm had regular appearances on shows such as Judging Amy and Desperate Housewives, which had him appearing next to John Slattery. Rahm's character was kind, empathetic, and caring – a perfect foil for Don Draper, despite how many similarities the two characters found they had.