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When I attended my first Seinfeld trivia night back in December, I never anticipated the chain of events I’d set into motion: I’d interview the trivia host, Dave Oliver and we’d become fast friends; I’d write my most-read blog post ever based on that interview; I’d join Dave’s company, Trivia, A.D., as a consultant; and I’d help him host a Seinfeld trivia night at Tom’s Restaurant, a.k.a. Monk’s Diner from the show.

Still, none of the above is so unbelievable that you’d doubt it if I put it in a blog post.

Slightly more unbelievable, though, is that on the night of the Tom’s event, I’d find myself in an Italian restaurant a few doors down from the diner, explaining to Jeremiah Birkett (the guy who played oversleeping marathoner Jean-Paul Jean-Paul on Seinfeld) and Lou Cutell (who played Dr. Cooperman, a.k.a. The Assman) that in about a minute, I’d be bringing them down the block and through the front door of Tom’s for their surprise guest appearance in front of a crowd of 80 trivia players.

What separates Tom’s Restaurant from any other coffee shop or diner I’ve ever been to is, well, not much, actually. If I didn’t know it was “the coffee shop from Seinfeld”–or recognize the neon “RESTAURANT” sign on the outside–I never would have figured it out once I was sitting inside eating my grilled cheese and rice pudding at the counter.

There’s a blurb in the menu that mentions the diner’s famous connections, but it’s understated and easy to miss:

Tom’s restaurant on upper Broadway and 112th Street has been serving Columbia University and the surrounding communities since the 1940’s. Tom’s became a legend through Recording Artist Susan Vega’s “Tom’s Diner” Song and even more so after appearing repeatedly on the world famous Seinfeld TV program.

On the wall to the right, there are a few enlarged and framed TV Guide covers featuring Jerry, George, Elaine and Kramer. And in the very corner, tucked between the front window and the counter, is “The Kramer” portrait, which Tom’s sells as a poster for $12. I decided not to ask the owner–Mike, not Tom–whether anyone has ever bought one.

To the locals–for whom Tom’s closed its doors for two hours while the trivia was going on–it’s just a diner where they go sometimes for a cup of coffee and a piece of pie. A wi-fi-less place for Columbia students to take a study break. A rare NYC eatery that doesn’t serve alcohol and only takes cash.

As trivia teams started to file in, Mike checked names off his list of reservations. I asked him whether his place was usually this full on a Monday night. He smiled and shook his head.

The guest list for the evening was invitation only, based on those teams who had been to Dave’s Seinfeld trivia nights before. The list of team names read like a Kentucky Derby race card if Jerry Seinfeld owned all the horses: Spongeworthy, I Was in the Pool, Mulva, What About the Driver?, and the odds-on favorite, Why No T-Bone?

The pre-trivia buzz for an average Seinfeld trivia night typically carries the nonchalance of any weeknight happy hour. But at Tom’s, the atmosphere seemed a little more tense. As teams assembled and claimed their booths or spots at the counter, I gleaned bits of one team’s conversation as they quizzed each on the minute details of specific episodes. I even heard one woman say, “I was studying my flash cards last night,” with a straight face.

And when Dave read the first question–“In the episode, ‘The Doodle,’ Kramer and Newman wait all year long for the Mackinaw peaches. Where do they come from?”*–the diner grew eerily silent as everyone considered their answer, knowing any misstep, even on the first question, could cost them. It felt like we were proctoring the SATs.

Hoping to raise the event’s profile, Dave had reached out to the agents and publicists for every Seinfeld actor he could think of in the months leading up to the event. Who knew, maybe one of them would actually show up. While most were either out of town or simply too busy to come, many sent gracious and genuine responses as well as signed headshots to give away as prizes at the event.

Dave only told a handful of people that Lou “The Assman” Cutell was going to be there–just in case Lou had to cancel last minute–but he was clearly excited. Every couple of weeks I’d get an email or text to the effect of, “I just talked to The Assman on the phone for 40 minutes!”

Jeremiah “Jean-Paul Jean-Paul” Birkett’s appearance that night was a surprise even to Dave, who explained that in earlier conversations with JPJP’s “people,” it seemed as though they didn’t want him doing anything without an appearance fee. But Dave’s shoestring budget didn’t have room for anything like that, so he crossed him off the list and moved on.

Outside the context of a Seinfeld trivia night, it might be hard to place Jeremiah Birkett’s face. He’s a Caribbean guy in his early forties and in good shape, walking around Manhattan’s Upper West Side in a fitted black t-shirt, a leather jacket and jeans. But inside the four walls of Tom’s, even 16 years after the Jean-Paul episode (“The Hot Tub”) originally aired on NBC, he was recognized instantly as Jean-Paul, even before Dave could announce him.

I led Lou in next, holding up the famous ASSMAN license plate out in front of him to help people connect the dots. He got an equally warm reception, after which Dave handed him the microphone to guest host the final round of questions–all of which referenced the episode in which he appeared, “The Fusilli Jerry.”

A professional performer for decades, Lou looked over at Dave as if to say, “What should I say?”, then proceeded to tell a couple of stories about Life After Assman which all ended similarly: “I’ve been in over 70 films, I’ve done Shakespeare on Broadway [yada yada yada] but I’m still remembered as The Assman!”

Lou then read the last round of questions, pausing comically in disbelief every so often to scratch his head and say things like, “Who would know this stuff?”

After the round was over, a few of us feverishly graded the answer sheets and tallied up the scores to determine a winner. Jeremiah bought us a little time, following Lou’s lead and telling a story about being hassled at the airport a few years ago on his way back from Amsterdam with his wife. A security guard looked at him funny for a few moments until realizing who he was, then proceeded to point at him, shout “Seinfeld! Seinfeld!” and eventually let him pass.

When it was time to crown a champion, Why No T-Bone? had edged out Spongeworthy by a single point to win the night. It was retribution for Why No T-Bone?, who has won nearly every one of Dave’s Seinfeld trivia nights but finished second in his 2010 Seinfeld trivia tournament.

Once Tom’s cleared out, Dave sat down–for the first time all night–with those of us who’d helped him throughout the event. As we sat there eating burgers, fries, and root beer floats, something seemed eerily familiar about a few friends sitting in a booth, having a conversation about nothing.

The next morning, Dave looked in his bag and discovered Jeremiah had autographed a head shot for him. It read, “Thanks Dave, you son of a bitch.”

*The Macinaw peaches came from Oregon. Several teams got this one right.
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It’s a Monday night in December and I’m sitting in a bar called Mulligan’s in Hoboken, New Jersey, waiting for my buddy Mike to claim the bar stool I’m saving for him. I lived in Hoboken for three years during my mid-20s and spent a lot of that time in bars, but I can’t remember ever seeing Mulligan’s this packed on any night of the week, no less a Monday.

The crowd, which is about 90% dudes, is there for the same reason Mike and I came out: It’s Seinfeld trivia night.

When the trivia host hands us our answer sheet for Round 1, I examine it carefully. It’s made up to look like the cover of a Penthouse magazine–a noticeable departure from the nondescript answer sheets you might find at other trivia nights. The blank white answer spaces, labeled 1 through 10, are strategically placed to cover the otherwise exposed cover models underneath (pictured below). In the bottom right corner, I notice the magazine is addressed to fictitious Seinfeld “dentist to the stars” Dr. Tim Whatley, DDS, who in one episode had an adults only dental practice and a waiting room stocked with adult reading materials.

Not your average answer sheet.

Mike and I are confident going into the first few questions. Between us, we’ve seen every episode 20 or 30 times in reruns. (I’d learn later that our host estimates he’s seen each episode at least 200 times.)

We keep pace with the leaders for the first few rounds, including a perfect 12 out of 12 in Round 2, attributing quotes from the show to the characters who said them. But by Round 4, matching obscure character names to their pictures, and the final round, made up entirely of questions about the “Festivus” episode, we’re toast.

We finish in seventh place. Our only consolation prize is the small laugh we get from the other players when our team name (To See Ramon?) is read aloud.

Still thinking about Seinfeld trivia the following morning, I reached out to Trivia, A.D., the company that put on the event, via Twitter. I wasn’t really sure what I expected to find.

But five days later, I’m sitting in Trivia, A.D. co-founder Dave Oliver’s living room in Hoboken, listening to him tell the story of how the company came to be.

This place looks like The Max from Saved by the Bell! How cool would it be if they had 80s trivia here?

For friends Amy Gerson and Dave Oliver, that epiphany came in May 2009 over drinks and tater tots at their favorite neighborhood haunt, Big Daddy’s on Manhattan’s Upper East Side. Big Daddy’s is an 80s-style diner that doubles as a watering hole for locals, which Oliver describes as “like Johnny Rockets but less cheesy.”

Half-jokingly, they bounced the trivia idea off each other for 10 or 15 minutes, after which Gerson (who freely admits, “I have a big mouth”) approached the manager on duty that night about co-hosting a trivia night with her friend Dave at Big Daddy’s, eventually getting in touch with the restaurant’s general manager.

He said yes.

Management didn’t know what to expect as far as turnout, so they set aside a space for Gerson and Oliver in the back of the diner to hold about 25 people. Big Daddy’s email-blasted their customer database to alert them about the event, and Oliver used his graphic design background to create an eye-catching flyer to hang inside the diner.

After just a few days of promoting, Big Daddy’s had 110 reservations lined up.

That first night went well–so well, in fact, that the nascent trivia hosting team was invited back to do 80s pop culture trivia at Big Daddy’s Gramercy location, and later to host more trivia nights at those locations as well as as at two Duke’s locations (owned by Branded Restaurants USA, the same people who own Big Daddy’s).

Before they knew it, Trivia, A.D. (named for Amy and Dave) had become a four-nights-a-month part-time job.

When Oliver approaches a potential client (i.e. a bar) about hosting a trivia night, they typically request “regular” or general trivia. But when one of his Friends or Saved by the Bell trivia nights brings in 80 to 100 people on a Tuesday night, that’s all the convincing they need.

The concept of a themed trivia night isn’t unheard of, but general trivia–topics like current events, geography, music and sports all rolled into one–is far more common in bars. For Trivia, A.D.’s events, though, people aren’t there simply by happenstance; they show up specifically to play trivia about their favorite TV show or movie because they’re passionate about it.

That passion is never more apparent than when Oliver hosts Seinfeld trivia nights, which he started in July 2009. In fact, Oliver says Seinfeld is one of his three passions in life (the other two are baseball and Pearl Jam), but there’s one couple who might love the show even more than he does.

“To date, we’ve won Seinfeld trivia 17 times,” says Jamie Sclafane, who plays under team name Why No T-Bone? with her husband, Dave. They’ve been attending Trivia, A.D.’s Seinfeld trivia nights since September 2009.

(For some more of Trivia, A.D.’s funniest Seinfeld trivia team names, see the comments section below.)

“We had been waiting for something like this for a long time,” says Sclafane. “When I saw the flyer, I immediately called Dave and was like we need to go to this!”

Why No T-Bone? placed second at Trivia, A.D.’s 2010 Seinfeld Trivia Tournament, which took place over three weeks in July 2010 across four Big Daddy’s and Duke’s locations. “The amount of work and detail [Oliver] put into the … tournament was incredible,” says Scalfane.

Each team who made the tournament “finale” received a Seinfeld themed gift, such as a giant marble rye or a box of Jujyfruits. “He also made … a giant clown check made out to The Human Fund and the sign to mile marker 114 for the highway Kramer adopted,” Sclafane says, “which we proudly hang in our dining room.”

Jamie and Dave Sclafane at Trivia, A.D.'s 2010 Seinfeld Trivia Tournament.

Looking to expand beyond bars and restaurants, Trivia, A.D. hosted a “Festivus”-themed Seinfeld trivia night at Comix comedy club in December 2010. Comix advertised the event in the New York Post and Oliver designed inserts promoting the event to put in the playbills for Long Story Short, the one-man show starring Colin Quinn and directed by Jerry Seinfeld.

Long Story Short donated 16 tickets to their show plus some Seinfeld memorabilia for the winners. Unlike previous Trivia, A.D.-hosted trivia nights, Comix sold tickets to the event ($15 plus a two-drink minimum), but still drew an impressive 125 people.

It’s easy enough to Google “Seinfeld trivia questions,” copy and paste the best ones, and pass them off as your own at a trivia night. But that’s not Trivia, A.D.’s style.

For Seinfeld trivia in particular, Oliver has a database of thousands of questions and answers and says he knows where to find just about any scene for any season within his Seinfeld DVD collection. (I detect a hint of pride in his voice when he tells me this.)

So, if I go to one of your Seinfeld trivia nights this month, and then I go to another one six months later, will I get any of the same questions?

No repeats, he guarantees, not at any of his trivia nights.

As we’re chatting, Oliver’s wife, Kara Oliver, stops in to tell her husband that she’s got a friend “who knows a guy who was in the Pez episode who owns a bar.” He appears to make a mental note to track down that lead once I’ve left.

While Seinfeld trivia is Oliver’s forte, he’s getting more comfortable writing questions and hosting trivia nights for themes in which he’s not as fluent.

“If you’re gonna host, you better know your stuff,” says Oliver. “Die hard fans pick up on that.”

Trivia, A.D. gets tons of requests for new themes. “Right now people want Scrubs trivia.” Oliver’s even heard requests for Little House on the Prairie trivia. (Do not look out for that one at a bar near you in 2012.)

“My favorite part of any trivia night is when we announce all the themes we do and hearing people’s reactions,” says Kara, who has hosted Trivia, A.D. events for Jersey Shore, Mean Girls, Mad Men and Caddyshack. “They get so excited to hear their favorite show or movie.”

Other Trivia, A.D. pop-nostalgia themes have included Star Wars, Beverly Hills 90210, Back to the Future, Sex and the City, and more recently, Arrested Development and Harry Potter. Oliver’s always got his ear to the ground for the next pop culture phenomenon that could make for great for a trivia night.

Just a year and a half after its inception, Trivia, A.D. had taken greater strides than Oliver and Gerson had ever imagined it could, but a series of bad breaks in the first half of 2011 left them wondering whether they’d taken it as far as it could go.

This past February, Oliver hosted a Seinfeld trivia event at Gotham Comedy Club, hoping to repeat the success of the Comix show. But a couple of factors were working against them this time–namely, it was the Monday night after Super Bowl Sunday–and the event drew just 40 people.

And in June, Trivia, A.D. and Big Daddy’s mutually dissolved their long-standing trivia arrangement; the two sides are no longer affiliated.

But Trivia, A.D. has rebounded, adding new venues to its roster in New York and New Jersey, including Croton ReservoirVillage Pourhouse, and Liberty Bar, and it currently has trivia events booked through March 2012.

Without giving too much away, Oliver hints at multi-city expansion beyond the New York metro area, and he’d like to further experiment with trivia events outside of bars and restaurants. “I have big plans,” he says.

Well, how’s this for big plans: On January 30, Oliver will host a Seinfeld trivia night at Tom’s Restaurant. If that name doesn’t sound familiar, it’s because fans of the show may know it better as Monk’s Diner, the coffee shop where Jerry and the gang spent an obscene amount of time during the show’s 10-year run. (Monk’s is based on Tom’s.)

Though the Tom’s event is already booked to capacity, Oliver is always looking to add the finishing touches. He has reached out to every Seinfeld actor he can get a hold of to get them involved in the event, from Bryan Cranston (Tim Whatley) of AMC’s hit series Breaking Bad to Patrick Warburton (the face-painting David Puddy) of CBS’s Rules of Engagement.

And if Jerry Seinfeld himself happens to show up at Tom’s that night, you can bet there will be a spot waiting for him in his old booth–there might even be room for three of his closest friends.

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