Early career

Lassiter was born Robert Henry Glodowski in Camden, New Jersey and raised in Collingswood, New Jersey, where he lived until dropping out of high school in the middle of his junior year and running away to New York City. He then wandered the United States doing odd jobs until arriving in 1970 on St. Thomas in the U.S. Virgin Islands.^[1]

A sales representative from a beautiful music radio station heard Lassiter's voice in a bar in Charlotte Amalie in the Virgin Islands one afternoon and immediately suggested he apply for an on-air job. Lassiter was soon hired as a music disc jockey at the salesman's station, WESP-FM, signing on September 1, 1970, under the air name of "Ron Scott."^[2]

He would move from there to beautiful music and progressive rock stations all over the country: WOUR-FM in Utica, New York; WOWI-FM in Norfolk, Virginia; WEZS-FM in Richmond, Virginia; and WJOI-FM in Pittsburgh.^[1] After his first marriage in 1972, he legally changed his name to Lassiter.

In 1981, Lassiter was working as a country music DJ at WKQS-FM 99.9 in Miami under the name Bobby Clifford when he heard talk-radio giant Neil Rogers on WINZ (940 AM). Rogers became Lassiter's mentor and idol, whom he followed into talk radio by taking a late-night weekend slot at Miami's WGBS-AM (710) in 1984. (Lassiter apparently intended to continue as Bobby Clifford on WGBS, but in preparing for his debut the station prepared promos and announcements using the name "Lassiter" without asking; Lassiter was forced to use his real name on the air.) Rogers heard Lassiter on WGBS and liked what he did, urging his own station—in a relentless, on-air campaign—to hire the newcomer. WINZ did hire Lassiter as a weekend host, but fired him in December 1985 when he uttered a profanity on the air.^[3]

Tampa: WPLP (1985–87) and WFLA (1987–89)

In September 1985, Tampa Bay's first all-talk station, WPLP-AM, lured Lassiter to Tampa with his first (low-paid) full-time position on weeknights. (At the time he was still working weekends on WINZ and doing fill-ins at WPLP; the station intended to move Neil Rogers from nighttime to day and, until Lassiter was fired, was grooming him as Rogers' replacement.) He took over WPLP's afternoon drive time slot on September 23, 1985. Lassiter recalled on the air that the station initially offered him $12,000 per year, which he turned down, eventually accepting a comeback offer of $18,000 when Rogers suggested he take the job as training for doing talk radio every day. (He later admitted faking his resume to get hired at WPLP, claiming to be a graduate of the University of Pennsylvania.^[4])

Although Lassiter's Miami career was not to be, he soon took Tampa by storm with his confrontational and deliberately offensive style, quickly rising to the top-rated talk program in the market by an enormous margin. He was, in fact, the second-highest-rated radio show in the market, bested only by Cleveland Wheeler and Scott Shannon's Q-ZOO on WRBQ-FM.^[5]

Lassiter redefined AM talk radio in Tampa Bay, asserting himself as an on-air bully who targeted Christians, conservatives, the elderly, and virtually everybody else. As he himself would one day describe:

A dozen years ago when I came to this town, talk radio was really quite amusing. ... It was basically old men talking to older men. ... Some exciting shows I heard in this market were things like, "If you know anybody famous, give me a call." And that was it. And the guy just repeated it over and over and over again, and got one call in an hour from somebody who knew one of the Harmonicats! ... Another show that I heard in this market was "What's your favorite vaudeville theater?" Another ... about once a month: "I own a Corvette. Do you own a Corvette? Give me a call if you do. What do you think about Corvettes? Would you like to own a Corvette? Did I mention that I owned one?" And he'd get two calls an hour. And I came in and sat down, and said "Ronald Reagan's a moron! And an idiot! You'll piss on his grave one of these days!" And the old people went berserk. Absolutely berserk!^{[2](1:22:34–1:24:00)}

Instead of a market for the retirees who formed much of the area's population, Lassiter made talk radio a young listener's medium: kids and young Baby Boomers would listen to hear Lassiter torment the old people. In the process, they would join in on the conversation and find themselves lambasted as well.

Lassiter's ratings and reputation were such that the biggest AM radio station in the market, WFLA, hired him away from WPLP for substantially more money in mid-1987. At FLA Lassiter joined the ranks of the golden age of Tampa talk radio, with such personalities as Dick Norman, Tedd Webb, and Liz Richards, and maintained his ratings supremacy to that local competition. Indeed, while Lassiter had pulled upwards of 7% shares at WPLP — which by itself made him the number one talk show in Tampa Bay — at WFLA he rose to 8 and 9 shares, at a time when the entire talk-radio audience in Tampa Bay was roughly a 10 share of the market.^[6]

Chicago (1989–91)

By 1989 Lassiter had become something of a sensation in the broadcast industry, appearing on national television and creating a demand for his talents in the largest markets in the U.S. WABC (AM) in New York made an offer in 1988, but WFLA would not let him out of his contract. (The slot at WABC eventually went to Rush Limbaugh instead.) Ultimately he was won over by WLS (AM), the Capital Cities/ABC radio hub in Chicago, who offered him a five-year, $1.05 million contract for the afternoon drive timeslot.^[7]

Lassiter's tenure at WLS was uneasy from the start: the CapCities executives behind the station micromanaged to an extreme degree, and were anxious to cultivate a friendly, inoffensive image, which ran completely counter to the type of radio that Lassiter did best. Members of management were waiting outside the studio on Lassiter's first night at WLS (23 August 1989) to give him a laundry list of things he had done that they did not want on their airwaves. Lassiter felt that since CapCities executives knew of his work before they even asked for a job interview, they knew perfectly well what kind of on-air personality they were getting. Lassiter deeply resented their sudden desire to rein him in.

Rather than change the style that had attracted WLS to him in the first place, Lassiter asked to be let out of the contract. The station refused, touching off what Lassiter called "open warfare" between WLS executives and their new employee. Their attempts to censor him only intensified his efforts to insult and infuriate his audience (and employers) on-air, and led Lassiter to walk out in the middle of staff meetings off-air. One journalist wrote that

he was at odds with management from the first day. "They'd scream everyday and I'd scream right back at them." Even worse, they put the Mad Dog on a short leash, but he kept breaking the chain. When told to curb his usual vulgarity and verbal abuse, he developed a code of secret insults which sounded like glowing compliments, and made the list available to listeners. When he was forbidden from saying he'd ever lived or worked anywhere other than Chicago, he'd coyly carry on in mock ignorance with the callers that remembered him from Florida.

"Tampa? Can't say as I've ever worked there."

"Oh, Sure you did, remember WFLA?"

"WFLA? I can't say as I've ever worked there."

It confused listeners who knew better, and drove management insane.^[8]

By late 1991, both parties were exasperated; unimpressive Arbitron ratings did not ease tensions. Lassiter's five-year contract had an escape clause that gave WLS the option to terminate it at the end of 1991, and Lassiter was openly predicting that the station would do exactly that. In fact, they didn't even wait for the end of the year, removing Lassiter from the air following his afternoon broadcast on September 20.^[9]

Although he would remember his time in Chicago as "a two-and-a-half-year nightmare", the job did raise Lassiter's profile significantly; in 1990, he appeared on CNN's Crossfire as a representative of left-wing political talk radio.^[10] In December 2005, Lassiter would later point out that - more than fourteen years after he was thrown off the air - he was still on the FAQ page on the WLS website. Indeed, as of August 2007, Question 7 on that page is "Why don't you bring back Bob Lassiter/Larry Lujack/etc.?" . "Maybe you don't know much about Lujack, but to be mentioned in the same sentence with him and WLS is more than an honor", Lassiter said. "It is and always will be the highlight of my career."^[11]

Return to Tampa

Callers

Lassiter had no use for callers who agreed with him, often rushing them off the line so he could find someone with whom he could have a compelling fight. In fact, after his monologue and topic setup he would often tell people who agreed with him not to call, that he was only interested in opposing viewpoints that day; if he received callers who agreed with him anyway, he would immediately hang up on them.

Lassiter was willing to give equal time to those who disagreed with him, even if he would mercilessly lambast them afterward. Frequently, though, he had to force the opposition to speak their piece, cutting off their attempts at preambles, red herrings and ad hominem attacks and demanding that they answer the question at hand. If there was an exception to this rule, it was with the cranks and extremists: when he received calls from the religious fringe, conspiracy theorists, ideologues, even members of the Ku Klux Klan—he would let them have their say, even encouraging them to make outrageously offensive and marginal statements and thus discredit themselves.

In later years, Lassiter became known for "punishing" his listeners when they didn't call in. If he reached a point in the show at which the switchboard wasn't lit, rather than riffing or starting a new monologue to fill the time, Lassiter would allow dead air to sit in. He might hum "The Anniversary Waltz", drum his fingers on the console, or even be heard quietly dealing himself a game of solitaire. Sometimes he would adopt more creative punishments: one night in Chicago, when nobody would address his topic, Lassiter invited calls from Born-Again Christians who wanted to give their personal religious testimonies, and wouldn't allow any other callers.^[17] The message was, it was a call-in show, so it was callers' job to carry the program. Lassiter had no intention of doing their job for them. Occasionally, though, he would reward callers who annoyed him with absolute silence: in fact, on the night of August 2, 1996, Lassiter kept a caller on the air at WFLA without saying a word for 12 full minutes.^[18]

On the other hand, despite his unsparingly caustic demeanor and complete frankness, radio with Lassiter was in many respects a kind of free-for-all. At least once a week, Lassiter would do "open phones", letting people call in with whatever they wanted to talk about. At times, he would even bypass the call screeners and answer the phones himself—a format he called "Chat With Bob"—letting prank callers, and anyone who wanted to be on the radio at all, speak (although he would censor them if necessary). This would lead to an inordinant number of people calling in and flushing toilets or holding the receiver up to the radio to hear the show on the six second tape delay; Lassiter would frequently respond to these calls by mocking the lengthy period of time they would wait on hold (typically forty minutes to an hour) just to do something completely trivial.

Monologues

Although he was unpleasant and pointedly controversial, Lassiter was a careful and engaging orator, building his monologues and telephone harassment with masterful diction, phrasing, and dynamics. It was a strategy that worked: he himself often noted that the secret of his success was that even the many people who despised him couldn't help but listen night after night, year after year.

Lassiter was not shy about airing his personal life on the air: he shared extremely intimate details of his own childhood (including his parents' divorce and his subsequent estrangement from his father); his first marriage, including stories of an abortion and infidelities by both parties; his own history of recreational drug use; and the ups and downs of his radio career. "You probably know more about me than you do about your own spouse, unless you have a better-than-average marriage", he once informed his listeners. Listeners were also frequently treated to present-day anecdotes about himself and his second wife Mary (the former Mary Toensfeldt—nicknamed "Muffy" — who had been the business manager at WPLP during his tenure there), or his hobbies of astronomy, birdwatching, futures trading, and fiddling with his home computer. Often these were subjects he defaulted to when taking a break from "coliseum-style radio."^[19]

Stunts

Lassiter was also famous for the hoaxes and stunts he pulled on the radio. At times he told his audiences that he would dunk a kitten into a bucket of water live on the air until the board filled with calls, or that he was now forbidden by broadcast-decency advocates from having any even remotely controversial content on his shows. One Friday in the mid-1990s, he and the entire staff of WFLA convinced listeners that he had been pulled from the air by panicky management while substituting for another host, told them that there would be a major announcement about his future during his regular timeslot on Monday, and when listeners tuned in he was back on the air to rub their nose in their own gullibility.