Shepherd was born in Memphis, Tennessee to William Jennings Shepherd and Patty Shobe. Named after her grandfather Cy and her father Bill, Shepherd won the 1966 "Miss Teenage Memphis" contest at age 16, and the 1968 "Model of the Year" contest at age 18, making her a fashion icon of the 1960s, resulting in fashion modeling work through high school and after.

She quickly made a name for herself as a curvy 'real woman', which was a departure from the trend at the time of Twiggy-type waifs. This led to regular work as a magazine cover girl, and according to Shepherd's autobiography, it was a 1970 Glamour magazine cover that caught the eye of film director Peter Bogdanovich. His then-wife Polly Platt, however claimed, that it was she who upon seeing the Read more...

Shepherd was cast opposite Charles Grodin in The Heartbreak Kid (1972). She played Kelly, the beautiful, sunkissed young woman whom Grodin's character falls for while on his honeymoon in Miami. Directed by Elaine May, it was a critical and box office hit, showing off comedic talents.

Also in 1972, Shepherd posed as a Kodak Girl for the camera manufacturer's then ubiquitous cardboard displays.

In Read more...