Brewster's first job in entertainment was as MC for a teenage radio program. Work in commercials, fashion commentary, and even weather programs soon followed. In 1956, Brewster was the announcer on The Ina Ray Hutton Show, a variety program on NBC television. On Maverick, Brewster's character is a gorgeous gambling con artist who often affects a southern accent but is ultimately likable. Brewster first played the character in a 1956 episode of Cheyenne entitled "Dark Rider" before appearing opposite James Garner in the third episode of Maverick, "According to Hoyle". Her other Maverick appearances include "The Savage Hills" with Jack Kelly, "The Seventh Hand" with Garner, and the famous "Shady Deal at Sunny Acres" with both Kelly and Garner. Writer/producer and series creator Roy Huggins had given her character his mother's maiden name. Brewster played Miss Canfield on Leave It to Beaver for the first season on CBS in 1957-1958 and for the 1980s television revivals. Brewster appeared in the show's pilot, "It's a Small World," as Miss Simms, a secretary with a dairy company, and in four regular season episodes as Miss Canfield. In Episode 1 she appears in the credits as "Diana Brewster", a mistake which was corrected in her next appearance in Episode 8. Brewster was replaced by Sue Randall as "Miss Landers" on the second season of Leave It to Beaver. In 1957, she co-starred with George Montgomery in the western film Black Patch, playing his former and future love interest. On January 31, 1959, Brewster played Lisa Caldwell in the episode "Runaway Train" of NBC's Cimarron City western television series. Also in 1959, Brewster appeared in The Young Philadelphians playing the mother of Paul Newman's character. She made almost fifty appearances in various other television and film roles, including episodes of Crusader,, Tombstone Territory, Tales of Wells Fargo and Harbor Was Command. In 1959, she played the girlfriend of Ronald Reagan's character in an installment of the General Electric Theatre anthology series, "Nobody's Child", and portrayed Marian Dell in the episode "Law of the Badlands" of the syndicated series Frontier Doctor starring Rex Allen. In 1960, Brewster had a starring role as Wilhelmina "Steamboat Willy" Vanderveer in The Islanders, an hour-long adventure series set in the South Pacific, with William Reynolds and James Philbrook. That same year, she also portrayed the titular role in "The Lita Foladaire Story," an episode of Wagon Train with Ward Bond and silent film star Evelyn Brent, in which Brewster's character had been killed before the start of the show, with her sections of the story posthumously depicted in flashbacks. Brewster subsequently guest starred on Empire and in The Rifleman episode, "Jealous Man" in 1962; on The Dakotas in 1963; on the 1963 Perry Mason episode, "The Case of the Potted Planter", and in the premiere episode of Kentucky Jones. Brewster appeared several times in flashbacks, uncredited, as the murdered wife Helen Kimble in The Fugitive. She appeared in two episodes of Death Valley Days, in a 1966 episode of Family Affair, and in an installment of Ironside before retiring. She reappeared in four episodes of The New Leave It to Beaver.
Death
Diane Brewster died from heart failure in 1991, aged 60.