Several of those in attendance were Dempster’s friends since elementary school, and later went on to be in bands with him. “We got together and told stories about Scott,” said guitarist Steve Connelly, who played with Dempster for several years in the popular ‘80s/’90s band The Headlights. “It was a sad time, but a nice time. The spot where we were, at the end of Turner Street, was where Scott and his friends used to hang out as kids, smoke pot and drink beer.”
The memorial continues on Tuesday, Feb. 7 with a Celebration of Life honoring Dempster at Ringside Cafe, now located at 350 1st Ave. N in downtown St. Petersburg. Connelly stepped forward to organize the live music, which will include performances by such old-heads as Bill Daniel (Peace of Woodstock), Danny DiPietro (The Headlights), Ed Woltil (Mad For Electra), Ricky Wilcox (Deloris Telescope), Walt Bucklin (Ronny Elliott & the Nationals), Ralph Martin, Bob Leichner, Dotti Leichner, and Connelly himself. Others may be added.
“Scott’s all-time favorite movie was ‘The Last Waltz,’” said Faune Walker, Dempster’s former girlfriend who took the lead in putting together the Celebration of Life. “We’re sending him off with his own Last Waltz.”
Dempster grew up in Clearwater and, like so many kids of his generation, fell under the spell of the British Invasion rock of the Rolling Stones, The Beatles, The Animals and others. “Experiencing this new music and all the pandemonium that surrounded it drew us into the point where we eventually crossed the line from being fans to learning to play an instrument so we could emulate our new found musical heroes,” emailed Daniel, Dempster’s childhood friend and a member of Peace of Woodstock, the tribute band that Dempster was once part of.
Dempster was happy to hold down the bottom end for whatever unit he was part of. “Scott wasn’t a virtuoso; he wasn’t even an accomplished musician,” Connelly recalled in a phone interview. “But he had the best bass tone. In The Headlights, I wrote his bass parts and showed him what to play. He’d learn them note-for-note and play the same thing consistently every night. That was a good thing when you had someone like me who basically never played the same from one night to the next. He had this pure love of being onstage and playing rock ’n’ roll.
“He was a rocker,” Connelly continued. “He loved the Stones. Scott never got into jazz, despised prog-rock. If you asked him about Yes, he’d say ‘No.’”
Added Steve Robinson, another member of the Headlights, via email: “It’s interesting to me that while many of us suffered from a little burn-out over the years, or became disillusioned with what is left of the music business, it appeared that Scott never really seemed to become jaded by it.”
Dempster was extremely well liked in the Tampa Bay music community. Musicians described him as an ideal bandmate, easygoing and quick with a smile. He was with The Headlights from the early ’80s to the mid-’90s. Its last and most successful iteration—a quartet that blended power-pop with jangle, folk and a dash of country—proved to be one of the Bay area’s most historically successful bands. The foursome won the Willie Nelson/Wrangler Music Invitational in Austin in 1986, which earned them recording sessions at Nelson’s recording studio.
Major labels made overtures to The Headlights, but—in an all-too-familiar narrative—nothing came of it. The band split not long after. The quartet has staged several reunion shows over the years. “Whenever we got together for one, [Scott] just had a glow about him,” Robinson wrote.
Dempster played a crucial, non-musical role in the group. Robinson explained: “Over the years, we were fortunate to have a few doors of opportunity open for us—some we barged into, some we tiptoed past, and some we slammed shut—but most of them were opened due to Scott’s incessant knocking.”
Connelly agreed: “All those great things that happened to us were because of Scott. The McGuinn thing was all because of him. He was the kind of guy who always tried to get backstage, meet people, make connections. In the late ‘80s, Scott got backstage at a Bob Dylan show and started chatting up McGuinn, and that started the ball rolling. That never happens without Scott.”
Sadly, in November no medical team was on hand as Dempster passed away in his Clearwater home, where he lived alone.
At the January get-together, people told stories and toasted their departed friend and fellow musician for about an hour. When the tributes were done, Connelly recalled, Wayne Shelor, another close friend, “picked up a bag of Scott’s ashes, checked the wind and dropped them into Clearwater Bay.”