In July, his father died at age 68 following open-heart surgery. Former Pistols bassist Ellen Gray Rutter, just 41 years old, passed away in early August after a long battle with breast cancer. And earlier this year, Howie went through a painful breakup with a woman he'd been dating since his divorce two years ago.
"It's been a crappy year," he says. "My father dies, who I was closer to than anyone I could possibly imagine. Then Ellen Gray. And a crappy breakup. It was like three strikes in a row."
The smashed windshield adorns the cover of "You Ruined Everything," the Pistols' recently released second studio album and first since 1997's "On Down the Track."
Howie had a real-life wrecked-up windshield experience while performing in Bahama, N.C. He returned to the band's van after the show to find part of a fallen tree that had relocated across the front of the vehicle. "I was like, 'Here we go again,'" he says. "So be it."
Howie, who formed the Two Dollar Pistols in 1996, is the lone original member. Off the top of his head, he says, he can think of about 15 people who've been Pistols at one point or another over the past 6 years. "An average of about three people a year," he estimates.
The original lineup mostly included guys who belonged to other bands: the Squirrel Nut Zippers' Jon Kempainen (fiddle) and Chris Phillips (drums); Jolene's and Johnny Quest's Bill Ladd (pedal steel); June's John Price (guitar); and the Gladhands' Pat McGraw. Only Phillips and Kempainen appeared on "On Down the Track."
Playing with musicians on loan, Howie knew early on would mean very little lineup stability. "You booked shows and hoped you'd have enough people to show up and play," he says.
The Two Dollar Pistols released their debut album in August 1997 on Scrimshaw Records, a division of Mammoth that folded when Disney bought Mammoth. "On Down the Track" included nine originals and covers of songs written by Howie heroes Harlan Howard, Roger Miller and Tom T. Hall.
A live album, "Step Right Up," followed in 1998 on Chapel Hill's Yep Roc Records, which also released the band's EP of duets with Lost Highway artist Tift Merritt in 1999 and "You Ruined Everything" in August.
Steve Howell, former guitarist for The Backsliders, joined the Two Dollar Pistols during the band's "Step Right Up" period. Howie gives credit to The Backsliders for giving him the confidence to follow through with playing country, a music he had loved since his youth.
Before Howie formed the Pistols, he served as a drummer in bands like Finger, a Raleigh band that took its cue from New York City punk rock circa 1977, and June, the only group Howie says he's played in that could sell out the Cat's Cradle, the legendary Chapel Hill/Carrboro nightclub. But a Backsliders' show in the early '90s set him back on the honky tonk trail.
"When I saw that, it gave me the inspiration," he says. "Here were these people playing traditional country music, other than Dwight Yoakam, and making it this vibrant thing. It was a really big deal."
The Two Dollar Pistols were part of a mid to late '90s Raleigh/Chapel Hill alternative country scene that boasted the likes of The Backsliders, Whiskeytown and 6 String Drag. None remain, and Howie thinks the reason why the Pistols have remained, at least in name, is because of his desire (or "limitation") from the start to focus on traditional country with less of a rock influence.
"I knew pretty much from day one what I wanted," he says. "You can probably hear elements of The Beatles or The Byrds on certain songs on 'You Ruined Everything,' but for the most part, it's still stone country. That may have helped that I haven't been divided in my goal to have a band that's a traditional honky tonk band at its core. I like R&B and The Beatles and The Byrds...but at the end of the day, it's still Charlie Rich or Lefty Frizell or Waylon Jennings, not The Band or Ray Charles."
The current lineup of Howie, guitarist Scott McCall, bassist Neal Spaulding and drummer Mark Weaver came together in late 1999. Howie says the Pistols are more like a real band now than they've ever been before. "They've stood by me," he says. "They completely made sacrifices for the benefit of the Two Dollar Pistols. We're much better spiritually, financially and everything else than we have been before."
Howie wrote most of the songs for "You Ruined Everything" shortly after the new lineup came together and the band fine-tuned them during live shows over the past few years.
The hard work obviously paid off. The album is the group's most accomplished effort to date and the first Two Dollar Pistols release to consist entirely of original songs. Howie's big baritone is at heartbreak-bringing best on songs like "You've Grown Tired of Me," "In My Mind" and the title track.
Howie says his voice has come a long way since his days in Finger, when he tried to sing like he was a member of the New York Dolls.
"I let myself sing naturally," he says, "not like I was hopped up on amphetamines and from Queens."
The 33-year-old says he's pretty certain this is the final version of the Two Dollar Pistols.
"My feeling is that there might not be a Two Dollar Pistols if and when this lineup fails...I like the way it sounds. If I were to change that, it wouldn't have that. After that, it would just be John. It would be the end of the Two Dollar Pistols. It's gotten too real to do anything else."