Let me hasten to add that I like late-period Jimmy too, brooding S&M Jimmy, just not as much. Note: It's not being a hater to say you like Picasso's blue period better than his cubism. Likewise, this.
One good place to look for my favorite Dean is Can-Am's Jimmy Dean Wrestling Special (1994), which features three JD ring matches (versus Billy Roberts, Cliff Conlin, and Troy Lucas), plus one JD-free match at the end (James Blond versus James Ryan, anticlimactic after three Jimmys, but still excellent).
In the first match, Dean and Roberts battle in thongs, Dean's, of course, the more colorful of the two. There's plenty of hair-pulling and acrobatics and out-of-the-ring strangulation. And both wrestlers end up slugging it out in the corner buck naked--Dean always struck me as the most comfortable of all Can-Am's talent wrestling nude (and pulling no punches while doing so). It's a tough fight, and one resolved with a jerk-off session at the end--Jimmy's long cock swathed in full untrimmed raccoon-coat '70s style--and in a happy coincidence Billy's cum shot coincides with the siren wail of an emergency vehicle outside the studio.
The second match is a personal favorite, as Cliff Conlin, another of my Can-Am idols, takes on Jimmy in enfant terrible mode. In demon red trunks, Cliff looks ready and able to cut the too-big-for-his-britches punk down to size. Jimmy, of course, goes for the dirty chokes, and Cliff, of course, smashes the blond bad-boy wafer thin. Excellent corner-work in this one, and enough flat-on-the-mat armbars and figure-fours to satisfy even me. It's more give-and-take than you might think, given Cliff's propensity for methodical dismemberment of his opponents. It goes three rounds, with 3 being the one where you fear for Jimmy's life. There's nothing I don't like in this fight, and little that I love in wrestling that's left out of it.
The third contest pits Jimmy against Troy, not the most charismatic of Can-Am's 1990s roster, but a dark, no-nonsense wrestler with the body of an Adonis. Here we see Jimmy, who might be mistaken for "all-nonsense," yet proving he's got the wrestling chops to go with his sass. Though this is a ring match, the action is pure, let's-go-hurt-each-other submission-style combat. Mere minutes into the battle, both men are huffing and puffing like powerlifters climbing Everest. For "wrestling purists," this is the Jimmy Dean you thought you'd never see. These boys bring wall-to-wall fuck-you-no-fuck-YOU to the ring.