|Portrayed by||John Slattery|
|First appearance||Smoke Gets in Your Eyes|
|Employer|| Sterling Cooper Advertising Agency |
Sterling Cooper Draper Pryce
|Occupation|| Head of Accounts Services, Senior Partner (Sterling Cooper) |
Founding Partner, Senior Partner (Sterling Cooper Draper Pryce)
|Ex-Wife|| Mona Sterling|
|Romantic Partners|| Annabelle Mathis|
|Parent(s)||Roger Sterling Sr.|
|Child(ren)|| Margaret Hargrove |
Kevin Harris (illegitimate)
Roger Sterling Jr. is a founding partner at Sterling Cooper Advertising Agency Advertising Agency in Manhattan, NY. Prior to that, he worked for the Sterling Cooper advertising agency. His father was one of the founders of Sterling Cooper in 1923.
Roger's past has been pieced together through his many recollections during the show. As the son of Sterling Cooper co-founder Roger Sterling Sr., Roger grew up in wealth. Always nautically minded, he claims to have sailed a tramp steamer to Hilton Head as a young man, though it was later revealed to have been a yacht.
As he often mentions, Sterling is a World War II Naval veteran. Prior to his deployment to the South Pacific, he was in an intense relationship with Anabelle Mathis, heiress to the Caldecott Farms dog food company. She ended their affair shortly before he shipped out, leaving Roger devastated.
In "Red in the Face", Roger's war recollections suggest he was the skipper of a ship running fuel between islands. Later in Season 4, however, he begins to tell Joan a story about being onboard a destroyer. For his time in the service, Roger was given a medal, and has since harbored a hatred for the Japanese.
Following the war, Roger began to work at his father's company, where he takes a dislike to fellow veteran Freddy Rumsen, believing him to have been a "coward" in the Signal Corps. The animosity disappeared when Roger learned Rumsen was only put there after having killed a number of Germans in combat.
- Annabelle Mathis, heiress to the Caldecott Farms dog food company. 
- Ida Blankenship, Don Draper's secretary. Roger had an affair with her when they were both young; he calls her the "Queen of Perversions."
- Jane Siegel, Don Draper's former secretary. Roger marries her between seasons 2 and 3.
- Joan Holloway, Sterling Cooper's office manager. See: Joan and Roger.
- Marie Calvet, Megan Draper's mother.
- Mirabelle Ames, 1 of 2 twins hired by Sterling Cooper as models for Cartwright Double-sided Aluminium. 
- Mona Sterling
Some time in the 1950s, Roger enters Heller's, a specialty shop dealing in fur coats to buy Joan a fur coat, where Don Draper is employed as a salesman. Roger comments on an advertisement for Heller's and Don states that it is one of his own. Roger hands Don a card showing that Roger works for an advertising firm. When Roger opens the box for Joan in a hotel room, he realizes that Don has included a portfolio; he considers Don to be "out of line" for including it.
A few days later Don runs into Roger in the lobby of Sterling Cooper, and tries to explain it away as coincidence. He asks Roger if he saw his work; Roger tells him that it was thrown away with the box. Don offers Roger a drink, and though it is 10am, Roger accepts. Over drinks, Don tries to sell Roger on the idea of hiring him. A few days later, Roger sees Don in the lobby again, waiting for the elevator. Roger is beside himself, angry that Don could not take a hint that he was not interested. Don stops Roger; while they board the elevator, he reminds Roger that he had hired Don the previous day. Don smiles as Roger appears confused about his lapse in memory.
On the Friday before Labor Day weekend in 1960, Sterling Cooper loses the Dr. Scholl's account. Roger attempts to cheer Don up by arranging for a pair of twins to spend the night with them. This results in Roger having a heart attack. The following October, Roger returns to the office, but has a second heart attack during a meeting with Lee Garner Sr., the head of Lucky Strike. As a result, Don is offered a partnership in Sterling Cooper. 
In 1962, Roger begins an affair with his secretary, Jane Siegel. He eventually leaves Mona, and proposes marriage to Jane. They married sometime in early 1963. Their happiness is short-lived, and their marriage causes friction between Roger and his daughter, Margaret, who asks that Jane not attend her wedding.
A New Company
When rumors of the purchase of Putnam, Powell and Lowe, parent company of Sterling Cooper get out in December, 1963, Don pushes Bertram Cooper and Roger Sterling, the original senior partners, to attempt a re-purchase of the company. After presenting an offer, they are rebuffed, until they hit upon an idea. Lane Pryce, the representative from PPL with authority over everyone at Sterling Cooper, agrees to fire the senior partners, thereby severing their contracts (including the no-compete clauses in their contracts) and join them in forming a new agency.
They secretly round up a list of clients loyal to them and steal important documentation that will assist the transition. They also quietly select the first employees: Pete Campbell, Peggy Olson, Joan Harris, and Harry Crane.
Sterling Cooper Draper Pryce (SCDP) receives word that Honda is looking for a new advertising agency. Roger blames the Japanese for the deaths of his friends during World War II and states that he does not want their business. In order to enable SCDP to proceed without Roger, Pete plans a meeting for Roger to attend; it would take place at the same time that the Japanese were in the office so that Roger would have no knowledge of their actions. In the middle of the meeting with the Honda executives, Roger bursts into the office and starts a rant, stating that they "don't want any of your Jap crap." After he leaves the room, the other members of SCDP apologize for Roger's rude behavior; in the folowing days, they realize that they have likely blown their chance when Honda does not send them a gift.
After the initial meeting with Honda, Pete accuses Roger of sabotaging the meeting because, if SCDP started doing business with Honda, they would became "less dependent on Lucky Strike and therefore less dependent on [Roger]." Roger rushes Pete, but Don steps in between the two men. After Pete leaves the room, Don tells Roger that Pete was right about this characterization.
Roger and Don plan on seeing the Muhammad Ali vs. Sonny Liston fight on May 25, though neither are happy about having to go with the Alcoholics Anonymous members, Freddy Rumsen and their client from Ponds. Don eventually cancels his plans to see the fight, much to Roger's dismay.
While Joan's husband is at basic training, Roger takes Joan out for dinner. While commenting on the condition of the neighborhood they are walking through, a man mugs them at gunpoint. Roger acts quickly, lowering his head and handing all their possessions over to the mugger. After the mugger runs off, Roger and Joan stop to catch their breath; they began to kiss and make love to one another while pressed against a fence.
Roger and Lee Garner, Jr., an executive at Lucky Strike, have dinner at a restaurant. When Lee requests to pay for the meal, Roger senses a problem; Lee apologizes, and tells Roger "It's over," that Lucky Strike is cutting ties with SCDP. He states that the board would like to consolidate the company to one firm, BBDO. Roger, visibly shocked, tells him that this is not the way that families treat one another; he points out all the times he had to lie to cover for Lee. Roger then attempts to haggle with Lee for a 30 day period in which to try and convince Lucky Strike to change their minds. Roger hands Lee's money back to him and pays for dinner himself. Later that night, he makes calls to old contacts, trying to track down new work for the firm.
Ken Cosgrove runs into an account executive from BBDO, who slips him the news. This starts a chain of events that eventually culminates in a meeting of SCDP's partners, blindsiding Roger, who has not told anybody about the break with Lucky Strike. Roger is forced to make a call to Lee; instead of talking to him directly, Roger fakes it by simply repeating his side of the conversation from his dinner with Lee. He is told by Cooper that he failed because he never took himself seriously, and neither did Lee.</span>
Roger promises to fly down and meet with Lee in person. The following day, he calls Joan and admits that he did not actually go out of the city, and that he is just a few miles away. Joan is understandably upset, and does not want to meet him. She promises to meet him later, but when they do meet she does not allow him to act on his impulses, telling him that she is "not a solution to [Roger's] problems. [She is just] another problem." They hug and he leaves, mentioning that the last time they were intimate was the night they got mugged.
Roger and the rest of the partners were frustrated with Don's full page ad, "Why I'm Quitting Tobacco". Roger thought of it as a good way to go down in flames. Bert mentioned the hypocrisy of including Don's name and not the rest of the partners. Don declared that he was able to get a good night sleep, to which Bert declared he was resigning from the agency.
During this time, Roger has been writing his memoirs, Sterling's Gold, in which he reveals that he once had a sexual relationship with Ida Blankenship, and that Bert Cooper was medically castrated by an incompetent doctor.
The following season, set in 1967, Roger became insecure about his lack of accounts and overall relevance in the agency. Friction arose between himself and Pete when Roger secretly monitored Pete's calendar to inject himself into client meetings.
Roger's unhappy marriage to Jane finally ended after they spoke honestly of their unhappiness while under the influence of LSD. Roger and Jane had sex on one occasion after they separated. Roger also entered into a casual affair with Don's mother-in-law.
In 1968, Roger uses information from an airline employee girlfriend to secure a pitch to executives from Chevrolet. After the pitch results in the Chevrolet account being secured, as well as a merger with rival agency, Cutler Gleason and Chaough, Roger seems to have reversed his insecurity within the agency.
Lane: "There's been a small adjustment to the scale of our Christmas party."
Joan: "Lower or higher?"
Lane: "Lee Garner Jr, will be joining us. I trust you'll make the appropriate improvements."
Roger: "We need to change its rating from convalescence home to Roman orgy."
- Roger accidentally invites Lee Garner Jr. to SCDP's Christmas party, Christmas Comes But Once a Year.
- Sterling is a World War II Naval veteran--a detail that becomes particularly relevant in Season 4's The Chrysanthemum and the Sword when Japanese company, Honda, approaches Sterling Cooper Draper Pryce for a potential client relationship.
Roger Sterling is rich and his wardrobe shows it. Roger's attire often features extras. He will wear a double breasted jacket or a vest. He accents his shirts with tie pins and cuff links.
Roger's wardrobe is often mature, but his adventures into the culture of the anti-establishment, including the LSD crowd and Hollywood, have caused him at times to update to his wardrobe with casual accessories such as an ascot or sports jacket.