Originally from a small farming town in Nebraska, he blossomed in high school, excelling at all sports and becoming a local legend. He was popular among the girls for his "movie-star looks". He chose Dartmouth college because of its sports program.
During the final game of the 1938 season with the Horned Frogs, pro recruiting scouts came to see Brady. However, an opponent fell on him, pulling out his knee. This injury ended his sports career before it began. As Brady was never a good student, he needed considerable help from his friend to barely manage to graduate.
Brady then moved to Bellview building in Manhattan to decide about his life equipped only with his good looks, reading want ads in the New York Gazette. Although he had no experience with the arts, he trained with a record and disappointingly auditioned for the chorus of a new Broadway revue.
When the National Bank noticed the rise of the 'masked man fad', the marketing team thought it would be a very interesting publicity prospect to be able to brag that a self-owned superhero would be protecting the customer's money. Designers were employed by the bank to make his costume. For aesthetic purposes and to raise maximum publicity appeal, the costume was extremely gaudy, with a large dollar sign on the front and a cloak that draped to the floor, especially liked by the test audiences.
Disappointed, he decided to answer an ad for the National Bank. He was the 14th who saw Misters Abie, Howe, Cheatem, and Dewey that day, and the only one who agreed to don the gaudy costume (although he had reservations about the cape restricting his movement) and work for the Bank.
That was until his employees decided that he should answer the ad from Captain Metropolis and Silk Spectre and join a band of crimefighters. Bill was reserved, but he was told that these were nothing more than actors like himself, and he should just "act like a real crime-fighter" although he still wanted to do his bit to make the country safer. In the audition, Bill was immediately recognized by Liberty Lassy. Despite his warning that he was not a real champion, C.M. and S.S. gladly accepted him in the team, as his presence would be an asset to their public profile.
A month later, the Minutemen had their first action against an alleged team of fifth columnists. Bill was inside their private tank along with C.M. and Hooded Justice. The mission was botched as the "saboteurs" turned out to be fireworks smugglers, but C.M. nonetheless gave a press conference about their success and a warning to America's enemies. This convinced Bill that the Minutemen were no different than his public persona.
Their next public mission was when the National Bank was being robbed by a gang of thieves and held hostages. The bank was surrounded by the police, but the Minutemen were there. Bill was forced by C.M. to follow the more experienced Nite Owl and Hooded Justice, as it was "his" bank. H.J. used a golden statue of Dollar Bill and hurled it on the thieves. Terrified, Bill watched as N.O. and H.J. fought the thugs and Bill brought back his former champion self; he rushed into the fray, using wrestling moves he had known.
His involvement with the Minutemen boosted his confidence. Due to his champion experience, he found in him the hero he pretended to be. Sometime between December 1939 and October 2, 1940, Bill decided to try his luck in the movies having collected enough earnings. He traveled to Hollywood, California, hoping to leverage his newfound fame in the Minutemen to forge an acting career, but finds out that he has become typecast due to his Dollar Bill commercials. He even tried his luck with Sunset Boulevard, low-budget studios, and even porn productions, but the answer was always the same. Dejected, he returned to New York, accepts his role as a bank spokesperson and ribbon-cutter, and rents an upscale apartment.
During World War II, Dollar Bill had a fancy deferment by the bureaucrats and was not enlisted. He continued to work as a mascot of the National Bank and appeared whenever a new branch was opened, usually with Mothman as a surprise guest.
That year, while attempting to stop a raid upon one of his employer's banks, his cloak became entangled in the bank's revolving door and he was shot at point-blank range before he could free it. He thought that the creep who injured him back in college was among the gangsters he hit. Hollis Mason speculates, "If he’d designed it himself he might have left out that damned stupid cloak and still be alive today."
His death was a highlight and was attended by his fellow remaining Minutemen, a police contingent, and bank representatives, with C.M. giving the eulogy. Dollar Bill's legacy, however, remained popular.
Bill was described as a God-fearing man. Hollis Mason notes "Dollar Bill was one of the nicest and most straightforward men I have ever met." He was seen admonishing the young Comedian about showing more respect to colleagues who were older than him. He had very negative views regarding women and homosexuality. When the Minutemen decided about the Comedian's fate after the rape attempt, Bill spoke in favor of the kid, mentioning his young age, and also Sally's provocative appearance. He also condemned Captain Metropolis and Hooded Justice's homosexual relationship, mentioning that thinking of it made him sick. Hearing about the Silhouette's death, he considered it a punishment for her lifestyle. Bill can be best described as a sexist, homophobic hatemonger who cares more about his beliefs than the lives of others.
Dollar Bill's clear commercial motivations (hired by a bank) are never commented on by his peers or the subsequent generation of vigilantes who all seem to regard him as a worthy hero; even the cynical Rorschach laments Dollar Bill's untimely death.
In every one of his appearances on-panel in Watchmen, Dollar Bill has a strong posture and is always smiling. However, Dollar Bill has no speaking lines in the entire series until Before Watchmen: Minutemen.