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Comedian Jim Florentine might well swing the biggest pair of brass balls in stand-up comedy—no small feat in a genre where bulletproof cojones are an occupational prerequisite. Most comedy and music fans know Jim from his duties co-hosting VH1’s That Metal Show, but Jim first crept into the pop culture limelight years before through recurring appearances on MTV’s subversive hit show, Crank Yankers. He has since appeared in myriad television shows and movies, and although Jim proceeded to win an Emmy in 2004 for his work on HBO’s Inside the NFL, his most enduring achievement may well be that this month, he released the worst comedy album of all time. On purpose.
On Awful Jokes from My First Comedy Notebook (Metal Blade, 2012), Jim revisits a notebook full of material he wrote in the early-90s, when he began his career in stand-up. The album’s title merits consideration for “greatest understatement of our time” because “awful” doesn’t begin to approach the agonizing depths of these jokes. These are the kind of one-liners that don’t cause you to simply cringe; they induce organ failure. Most surprising is that when Jim found the notebook during a recent move, he did not take it to Louisiana, burn it in a barrel full of gasoline and roadkill, seal the barrel and under the light of the moon, ferry it out to the deepest part of a remote swamp, drop it into alligator-infested waters, and on his way home, shoot the guys who sold him the barrel and rented him the boat, so that no living thing would ever know that something so depressingly unfunny ever existed.
Instead, in what has proved to be a brilliant turn, Jim walked the notebook into the recording studio, rolled the tape and read each horrible joke, one after the other, with nothing but a sterile studio silence hanging between gags, occasionally broken by Jim’s self-loathing observations, such as, “I wanna pull my eyes out right now…” Without the benefit of a live audience to chuckle, or in this case, groan, the 
jokes stand naked in their lameness. Which is precisely what makes the album so funny; as the bad jokes pile up like multi-car wrecks in a CHiPs marathon, head-shaking grimaces melt into the kind of breathy, involuntary laughter that afflicts people trying not to laugh. Like watching a man repeatedly knock himself in the head with a ball peen hammer, you cannot help but feel bad for him as he rattles off dud after dud, but ultimately the album’s secret ingredient is the underlying charm of witnessing a would-be comedian taking his first awkward steps in the business. It helps that in Jim’s case, we know the story has a happy ending.
The ballsy gamble that has paid off: Awful Jokes skipped onto the iTunes Comedy charts in its first week and has since enjoyed decidedly favorable reviews. Obviously, you don’t score record deals, win Emmys and land choice television gigs without putting in the requisite 10,000 hours of spine-cracking work, yet few realize that Jim Florentine was also the beneficiary of a notorious, and most unlikely mentor.
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Legendary guitarist “Dimebag” Darrell Abbott was the anti-Cobain. As Nirvana and the marauding grunge hordes eviscerated glam rock, Dimebag’s band Pantera released a trio of albums that injected heavy metal with a much-needed dose of vitality and swagger. With Dimebag supplying galaxy-sized guitar riffs and the rhythm section of his 
brother Vinnie Paul on drums and the dextrous Rex Brown on bass, Pantera perfected the recipe with singer Phil Anselmo, whose mercurial persona and panther-like moves pushed the band onto the biggest stages on the planet. Together, the four men pioneered what is now known as “groove metal,” a rubbery blend of Black Sabbath, ZZ Top and early Metallica that galvanized existing metal audiences and attracted legions of new fans through Pantera’s mainstream success. Nirvana dropped Nevermind in September of 1991, but by then, Pantera were already playing in front of a half million fans at the historic “Monsters of Rock” show in Russia.
Commercially and creatively, Pantera were unstoppable. In fact, with a manic global fan base and the gradual return to prominence of heavy metal, the only force strong enough to take down Pantera was ironically, Pantera. Amid accusations of drug abuse and an astonishingly public war of words, Pantera fractured into two bands, with Anselmo and Brown moving on to form Down and the Abbott brothers returning to Dallas to form the hard rock outfit Damageplan.
To this day, guitar players across many genres credit Dimebag as a critical early influence. He played with 
the eye-popping speed of Eddie Van Halen, all twisted up and wrung out with filthy Texas blues, creating unique rhythms and inventive hooks that shifted the way many guitarists approached their instrument. Offstage, Dimebag exuded a charm that magnetically pulled both fans and colleagues into his orbit. Spend a few hours with Dimebag and you’d leave with a friend for life and a brain-piercing hangover.
Tragically, Dimebag’s life was violently cut short in 2004, when a psychopathic gunman shot him down in cold blood as Damageplan were performing at a small club in Ohio. In addition to Dimebag, the gunman killed three others and wounded seven before a police officer slipped in through the back of the club and stopped the madman with a fatal shot to the face.
For his final send-off, Dimebag was buried in a KISS coffin donated by Gene Simmons, along with Eddie Van Halen’s original “Bumblebee” guitar.
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It was sometime around the release of Pantera’s 1992 masterpiece, Vulgar Display of Power, that Jim launched his stand-up comedy career. His boundary-shattering irreverence and laconic, Jersey-flavored delivery resonated with local audiences, and the comic soon began booking out of town gigs, one of which landed him in Dallas, headquarters of Damageplan. Jim was already one step ahead of them.
“I was doing the Improv in Dallas, and I knew (the Abbott brothers) were big comedy fans,” Jim explained to TNB Music. “See, when I’d go into a town and go on the local radio, if I knew that a rock star lived in that town, I would just keep talking about him. Eventually some friend of his would tell him, ‘Hey some comedian was talking about you guys on the radio and said you were going to come down to the club…’ That was my move.”
Consequently, during his Dallas radio spots, Jim enthusiastically professed his love for Pantera and his admiration of Dimebag Darrell, hoping word might trickle back to the band. To Jim’s surprise and delight, his campaign worked. As he prepared to take the stage that Saturday evening, the club manager pulled him aside to advise that the guys from Pantera were sitting in the very front. Peeking out into the house, Jim saw not just Dimebag, but the entire Damageplan band: Vinnie, vocalist Pat Lachman and bassist Bob Zilla, plus Dimebag’s girlfriend Rita and a posse of decidedly un-sober friends.
It was one of those “Be careful what you wish for” moments.
“I thought, ‘Holy shit,'” says Jim. “I look out there and see cowboy hats, friggin’ seventy-five beer bottles and like forty-five shot glasses on the table. I’d never met those guys before; they didn’t know who I was. This was before That Metal Show.”
The boisterous cadre of rock stars in the front row introduced a terrifying new level of pressure to the gig; which is one of the reasons Jim doesn’t drink before a show—so he can navigate such dicey contingencies. Drawing a deep breath, Jim took the stage and immediately threw a shout out to the band in the front row, evoking thunderous applause from the club. Pantera might have disbanded, but around those parts, the musicians were still as big as the Dallas Cowboys.
Standing up, Dimebag tipped his hat and waved to the crowd, and then presented a shot of Jaegermeister to Jim, saying, “Here you go, buddy!”
In a brave, but misguided effort, Jim protested, “Thanks, but I don’t drink before the show, but I’ll do that after the show.”
The reason comedy clubs impose a two-drink minimum on patrons is for these precise moments. The shack full of liquored-up Texans exploded into a hail of boos. Satisfied that the crowd were on board with his plan, Dimebag countered, “Well fuck that, you’re doing a double, then,” thrust a second shot into his hand and ordered, “Now drink that!”
Wisely, Jim took his medicine, barely managing to dodge a third shot. Satisfied that the comedian was adequately-fueled for the performance, Dime sat down and said, “Alright, alright, let’s go! Bring it!”
Although by his own estimation, he was “pretty fucking hammered,” Jim nonetheless delivered a show that so thoroughly entertained the band, that the Damageplan boys invited Jim to join them at The Clubhouse—a strip joint owned by Vinnie—where they drank into the wee small hours, with Jim and Dimebag holed up in the back room, talking about music and comedy for hours.
Dimebag regaled Jim with stories of Pantera and the vision for Damageplan; while they could have parlayed the Abbotts’ Pantera connection into some high profile opening gigs, Damageplan would instead hit the road just like any other new band, converting audiences one small stage at a time. Jim recalls Dimebag saying, “Lemme tell you something. We’re gonna start playing in the little clubs like we did back in the Pantera days, and I don’t care. Just remember this as a comic, man— it doesn’t matter if there’s three people in the crowd or a hundred thousand–you still fucking bring it, 150%, every time you’re on stage. Because those three people came to see you.”
From that boozy interlude, the two men forged an enduring friendship, taking an interesting turn years later, when Damageplan tapped Jim to open for them during a series of dates in Canada. One morning he’s telling a Dallas DJ about his love of Dimebag Darrell and the next thing he knows, he’s opening for the guy in another country.
One night on that tour, Damageplan decided to add a last-minute show to fill an open slot. When they arrived at the venue, members of the band were dejected to discover a modest crowd of 200 waiting—far short of the numbers that they had hoped to find. Dimebag was incensed; not at the turnout, but at his colleagues. Jim watched as Dimebag tore into his bandmates, “What the fuck? There’s 200 people that came to see us tonight! Instead of doing an hour and twenty tonight, we’re doing 2 hours! Fuck that, we’re doing 2 hours and ten minutes! These kids are getting a show!” True to his word, those 200 kids enjoyed a blistering two and a half-hour set that night.
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Jim Florentine paid his dues the old-fashioned way: through hard work, relentless touring and by persevering through those ego-smashing indignities known only to stand-up comedians. To suggest that he scored his Emmy or his TV career by any other means would be a terrible injustice.
Still, Jim is quick to credit Dimebag with infusing him with a much-needed measure of gratitude for the people who throw down their hard-earned cash to see him perform. Before their star-crossed friendship, Jim admits that the sight of a half-full or even three quarter-full club would leave him bitter and dejected, eager to finish the show and move on to the next gig. But that attitude disappeared one alcohol-fueled night in the back room of a Dallas strip joint. Eight years after his death, Dimebag’s words still ring in Jim’s ears when he takes the stage: “It doesn’t matter if there’s three people in the crowd or a hundred thousand–you still fucking bring it, 150%, every time you’re on stage. Because those three people came to see you.”
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