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He was voted Most Likely to Succeed, and in 1980, after he graduated from high school, Dunham gave himself a career goal of obtaining, within ten years, an appearance on The Tonight Show Starring Johnny Carson, which was seen as the "holy grail" for comedians.
By his junior year in college (1983–84), Dunham was making ,000 a year, and as word spread of his act, he landed featured spots opening for Bob Hope and George Burns, though he still perceived his act as raw, as he did not have any knowledge of standup comedy beyond his Bill Cosby albums.
The organizers of the Con VENTion eventually declared Dunham a "retired champion", ineligible from entering any more competitions, as other attendees were too intimidated to compete against him.
The Vent Haven Museum devotes a section to Dunham, alongside Señor Wences and Dunham's idol, Edgar Bergen.
Finally at the Ice-House in Pasadena in April 1990, after Dunham did the same segment, Mc Cawley informed Dunham that he would finally get his Tonight Show appearance. Upon sitting down next to Carson's desk, Dunham pulled out Walter, who told Carson sidekick Ed Mc Mahon, "Stop sending me all your damn mail." At the time, Dunham saw his Tonight Show appearance as his big break, but was frustrated at his parents' initial disapproval over Walter's use of the words "hell" and "damn", Dunham would appear on The Tonight Show a total of four times, as well as similar TV venues such as Hot Country Nights, appearing in one segment with Reba Mc Entire.
Dunham and Peanut appeared on The Tonight Show Starring Johnny Carson on April 6, 1990, alongside guests Bob Hope and B. This exposure helped make Dunham a large theater headliner, a rare accomplishment for a ventriloquist, but by the mid-1990s, his television appearances had dwindled, and with them, so did his stage audiences.
in various venues such as school, church, and during his job at Six Flags.
By his middle school years, he began to perform for banquets attended by local celebrities such as Dallas Cowboys quarterback Roger Staubach, having developed his style of lampooning those he performed for, using the puppets to say things too risque for him to say without them.
To maintain a connection with his fan base, he would use question cards that he had audiences fill out for his performances to build a database, which was tailor-made for the burgeoning World Wide Web.
By the fourth grade, Dunham decided he not only wanted to be a professional ventriloquist, but the best one ever.
Dunham has explained that, as an only child, he enjoyed being alone, likening his solitude to a "warm blanket" with which he could explore his own thoughts and ideas, which prepared him for the solitude of living alone when he later moved to Los Angeles as a struggling comedian.
At the end of 1988, Dunham was told by James Mc Cawley, a talent booker for The Tonight Show Starring Johnny Carson, that Dunham would be given a spot on the coveted program.
Though the 26-year-old Dunham was elated that his 10-year goal was arriving two years early, Mc Cawley later cancelled Dunham's appearance after attending, with Roseanne Barr, a public performance of Dunham's the day before Dunham's scheduled Tonight Show taping.
When he first arrived in Los Angeles, the comedy in his act bombed.