Don Draper = Dylan McKay When you think about it, Don Draper and Dylan McKay are pretty much the same character. Sure, the former is the middle-aged creative genius behind Sterling Cooper Draper Pryce and the latter is a rich teenager with a motorcycle. But they’re both mysterious sex symbols, betraying little about themselves and driving all the ladies wild. Don and Dylan have buckets of daddy issues and also seem to be smarter than everyone around them, occasionally given to making profound, impressive speeches. Also: While Don’s character pretends to be younger than he is, Dylan is played by an actor (Luke Perry) who is at least a decade older than the character is supposed to be. And need we mention each character’s substance abuse problems?
Betty Draper = Kelly Taylor Betty and Kelly are our archetypal all-American, blonde-bombshell princesses. Both have modeling in their past and they are ensnared in eternally on-again, off-again relationships with Don and Dylan, respectively. They may seem spoiled, but Betty and Kelly have both endured their share of pain. (Remember when Kelly got raped?)
Roger Sterling = Steve Sanders Entitled, fun-loving, womanizing rich guy — the description works equally well for Roger and Steve. Both characters are the life of the party and serve as a sort of comic relief. They could also probably use some help dealing with their anger management issues…
Peggy Olson = Andrea Zuckerman Smart and ambitious, with quaint, working class families, Peggy and Andrea both begin their story lines as socially awkward nerd girls. But over time, these hard-working writers gain confidence, excelling in their leadership positions and earning the acceptance and respect of their peers. Of course, it’s not all upward movement: Andrea and Peggy also give birth waaaaay before either was planning to.
Ken Cosgrove = Brandon Walsh These two are both go-getters and literary types — Ken writes stories for The Atlantic while Brandon excels as a student journalist. Although they’re generally well-liked, their talent and success makes them an easy target for the jealousy of lesser friends and colleagues.
Joan Harris = Brenda Walsh Sure, they may not be yellow-haired prom queen types, but Brenda and Joan have something even better — bodacious sex appeal and a superior sense of style. Both are great actresses (watch Joan pretend to be happy in her marriage!) who are also smarter than their friends and co-workers give them credit for. Joan and Brenda also have a serious knack for social engineering, manipulating situations to get whatever — and whoever — they want.
Pete Campbell = David Silver Pete and David: Young, scrappy, and sometimes too precocious for their own good. Prone to temper tantrums and bad hairstyles, it’s usually these guys’ big mouths that get them into trouble. (Remember the disaster that was David’s “relationship advice” radio show?)
Trudy Campbell = Donna Martin Prim, proper, and perhaps even a bit frigid, Trudy and Donna are your classic upper-class good girls. Both ladies are daddy’s girls who are (or, in Donna’s case, have been) saddled to immature guys who don’t deserve them.