When Marc Eisenberg entered the 9:30 Club’s annual holiday raffle in 2013, the pressure was on.

Eisenberg and his wife were planning to start a family and he saw his free time — time he often wanted to spend attending concerts — rapidly shrinking. The Shaw resident remembers thinking it was “now or never.”

“I was like, ‘I have to win this year, because I’m going to have a baby and I’m never going to be able to take advantage of it if we have a child,’” he says.

Eisenberg was looking to become part of a select group of locals who have won unlimited access to one of D.C.’s most beloved music venues. Every year during the holidays, the 9:30 Club collects donations for local organizations in exchange for the chance to win a free pair of tickets to every single show for a year. Participants would donate items, like canned goods or clothing, in exchange for raffle tickets.

Eisenberg, who is the executive director of the Washington Bach Consort and a “huge live music geek,” upped his donations each year in an effort to boost his chances.

In 2013, his efforts finally paid off. The now 50-year-old learned he’d won at the club on New Year’s Eve.

“Trombone Shorty was playing and they pulled my name out of the hat,” he says.

As the raffle enters its 20th year, the 9:30 Club is offering that grand prize to two winners for the first time: one from in-person donations and the other from monetary contributions online (a component originally introduced last year while the club was closed due to COVID-19.)

Eisenberg spent the following year seeing roughly 150 shows, with acts ranging from saxophonist Karl Denson and his band Tiny Universe to German electronic pioneers Kraftwerk. He even kept a blog where he wrote up each performance, including artists he might never otherwise see, and otherwise reveled in the freedom his grand prize winner status afforded him.

“I would just show up at the club with zero expectation, not knowing who I was going to see and there was no pressure,” he says. “If I liked it, I would stick around. If I didn’t like it, I would walk out the door. Even if I was a millionaire, I don’t think I would ever have that attitude.”

The raffle got its start in 2001. Donna Westmoreland, currently the chief operating officer of I.M.P. — which operates the 9:30 Club, The Anthem, and other area venues — suggested the idea, inspired in part by her time as Lilith Fair’s head of marketing and the touring music festival’s charitable contributions.

“We are in the business of having fun, and it’s nice, especially around the holidays, to channel some of that energy to good,” says Westmoreland. “And so, it was like, ‘Well why don’t we do this?’” The idea was a hit.

Todd Savitch had been going to the 9:30 Club for years and “became obsessed” with the raffle. In 2007, the fifth year he entered, he won.

“It was amazing to walk in there whenever I want,” says Savitch, an administrative assistant at a law firm. He attended 166 shows, going to the club as many as ten nights in a row to see shows he “just couldn’t say no to.”

Savitch, who is 52 and lives in Adams Morgan, already knew some of the venue’s employees, but he got to know more of the staff as he became a fixture there. (“When you’re in there for free, I was always tipping pretty well,” he adds.)

A lifelong music lover, Savitch attended his first show at 11 months old when his parents took him to see The Who (though he doesn’t remember it). He later worked for the now-defunct D.C. record label Fifth Colvmn Records.

As the winner of the raffle, he spread the wealth with friends and family, rotating his plus-one depending on their taste in music.

One night, he says, he took his mom to see Michael Franti & Spearhead, and she only planned to stay a little while. She ended up staying for the whole show, and the pair went to Busboys and Poets afterward for a benefit Franti was playing there.

“I think there was some big peace march the next day, so we ended up getting into that show and staying there until three in the morning,” Savitch recalls.

His favorite performances that year included Elvis Costello and Iggy Pop and the Stooges. But after a whirlwind twelve months of live music, Savitch says he felt “a little relieved” when it was over. It was nice to take a break.

Jayne Sandman, 2021’s winner, meanwhile, is still looking forward to using her tickets. Sandman, who says live music is a huge part of her and her husband’s normal social lives, had entered the raffle many times before. She donated money online last year and won while the 9:30 Club was still shuttered. She was told her prize would be good for a year from when the club reopened, and she attended its surprise, sold-out Foo Fighters show in September, her first indoor concert since the pandemic started.

“There wasn’t a lot of notice for the Foo Fighters show… and I remember that was the first time that I had taken advantage of using the pass,” says Sandman, who is co-founder and co-CEO of marketing and public relations firm The Brand Guild. “It was pretty awesome to know that I could do that.”

Her prize’s end date has since been extended until the end of 2022. She has told close friends that she’ll happily take them to any sold out shows they want to see (the prize is non-transferable and only the winner of the raffle can pick up the pair of tickets).

Sandman, who is 42 and lives in Bethesda, is particularly excited to see Australian indie-rocker Courtney Barnett in the new year, along with many other artists, provided the omicron variant of COVID-19 doesn’t upend those plans.

“Everything’s kind of a new risk matrix right now, so it’s tricky,” she says. “But I don’t know. I feel like live music is also–it’s like my fun time and my sanity, so I’m trying to carve out as many shows as I can.”

The raffle’s reach has grown over the years. This time, it will benefit seven local organizations including Capital Area Food Bank, Casa Ruby, and Thrive D.C.

Entrants can bring canned goods, non-perishable food items, and clean, gently-worn clothes to the club at 815 V Street NW during normal box office hours or at any show in December, or donate money online via BetterWorld.

Each item donated in person is worth one entry, with a limit of ten entries per day–though more than ten donated items are welcome. Every online entry is $5, with no limit on the number of times people can enter. Online donations close December 31 at 11:59 p.m.

The grand prizes aren’t the only ones up for grabs, either. The 9:30 Club will distribute other winnings from community partners, like a gift card to local cidery Anxo, a three-month membership at Balance Gym, and a tour of Union Kitchen’s commercial kitchen in Ivy City.

Grand prize winners, who will be selected at random and notified on Monday, January 3, can look forward to “concert heaven,” as Savitch calls it. “It’s a great prize for someone who loves music and it was a way to help the 9:30 Club help the community.