Derek Stricklin made OQL USA TOTW in weeks 3 and 4 of Season 19. The following interview was conducted while we drank bourbon and dined on Rabbit dumplings and Dirty Pasta at Butcher and Rye in Dahntahn Pittsburgh.
Tim: How did you first get into trivia as a hobby? What are your first memories of it?
Derek: I’ve been interested in trivia for a very long time. I watched lots of game shows as a kid, my local sports bar had a Buzztime game where you could borrow a handheld device and answer questions on the TV, and I did very well in middle school quiz bowl tournaments. That interest eventually grew into playing in online leagues and attending events like SporcleCon and Trivia Nationals.
Tim: When did you first get into OQL? What team did you join and what has the experience been like?
Derek: In 2025, my good friend and frequent bar trivia teammate Paul McLaughlin invited me to compete on his Quizzo Bowl team in Philadelphia, where I first met you. A few months later, you invited me to join Orphans of the Seven Kingdoms. OQL has been a very fun experience.
Tim: Losing to Sofa Kingdom in a tiebreaker in 2025 was one of the worst losses I have experienced as a trivia player. We have finished second three times in Quizzo Bowl which is soul crushing.
Tim: What other online leagues do you play in and what are your favorites?
Derek: I play in OQL, in QuiP on We Built This City on Quokk and Roll, and in LearnedLeague, where I’m currently an A rundler in Orchid. All of them are fun in different ways: QuiP has the look and feel of a virtual game show, OQL has an element of luck to it based on where each player is positioned, and Thorsten A. Integrity’s writing style in LearnedLeague feels like a perfect cross between brainteasers and trivia, leading to many “aha” moments when you finally figure out what he’s asking.
Tim: Have you ever been on a game show? Are you currently trying out for one?
Derek: I haven’t, but I’m a huge game show fan and I’d love to compete on one. I’ve taken the Anytime Test for Jeopardy! many times and had a virtual audition in 2024, and I also recently had an interview with the casting team of Trivial Pursuit.
Tim: Do you play live trivia at any bars in Pittsburgh? What is the scene there like? Also please tell us
about your experience in the city as a trivia writer.
Derek: All the time. There’s lots of great options in the city. Buzz Worthy Pub Trivia, Drew’s Clues Trivia, Liz Quesnelle’s games with Madcap Trivia at Hop Farm Brewing, and Paul McLaughlin’s games with Steel City Trivia are some of my personal favorites.
I’ve written bar trivia questions for almost ten years (it’ll officially be ten years next January). It’s a fun hobby that’s taught me how to read and write a question and caused me to learn about subjects I mightnot otherwise go out of my way to learn about, and I think it’s directly contributed to my success as a quizzer.
Tim: The online quiz leagues powers that be hurt me deeply because I have been trying for years to write for them yet get rejected at every turn. I feel very ostracized from a community I genuinely enjoy partaking in. I just want to be given a chance.
Tim: Did you attend SporcleCon or Trivia Nationals the past three years? If so, what was it like? How
has your overall experience with the trivia community been?
Derek: I attended SporcleCon in 2024 and 2025 and will be going to Schaumburg this year, and I also went to Trivia Nationals for the first time earlier this year. The organizers of these events do a great job of providing fun activities and opportunities to meet and interact with other attendees. It feels great to know that there are like-minded people who share the same enthusiasm I have for this hobby, and everyone I’ve met in this community has been very friendly.
Tim: What are your top five trivia/quiz highlights both as an individual and as part of a team?
Derek:
1.)In October 2025, I traveled to Las Vegas to compete in an event called Trivia: The Gathering. It
was basically a weekend-long Jeopardy! tournament in the hotel’s conference rooms. My
expectations were very low, but I made the semifinals and won several games against some
multi-day champions from the actual show. Some of the other players there even noticed my
performance and got me in contact with former contestants who have helped me improve my
skills.
2.) In 2023, I got to play bar trivia against Steve Perry and Victoria Groce—two quizzing icons who
also live in Pittsburgh—at Hop Farm Brewing. Their team won easily (I’d expect no less from
them), but it was an honor to get to play against two legends of the game. The trivia version of
playing a pickup game against LeBron or prime Michael Jordan, if you will.
Tim: Victoria once read a regular OQL game for one of my games and played against us in Quiz Nations. It was harrowing and thrilling for various reasons! Another unbelievable thing was her husband played on my OQL Regions team.
Derek:
3.) In 2016, back when Sporcle Live had a presence here in Pittsburgh, I won $300 in their regional
championship as a solo player. If I didn’t wager conservatively on the final question, I would have
earned first place, a trophy, and $1,000.
4.) Using bar trivia to make friends and build a support system when I was just a young ingénue (hi
Doug and Kristen!)
5.) At my first SporcleCon in 2024, I was placed on a scratch team mostly consisting of people I
never met before. We got all three of the 10-point wager questions correct and tied for 12 th place!
Tim: How many OQL Team of the weeks have you made and what stood out to you in the most recent
one?
Derek: The most recent one was Week 3 of Season 19, where I scored thirteen points, got five directs correct, and answered both questions correctly in the Bishop Sycamore/IMG Academy pair. Every game is truly a team effort, and I’m fortunate to get to play with some very talented players. The answers that they’re able to pull sometimes amazes me.
( Derek made TOTW in Week 4 but this interview was conducted before the results came out)
Tim: Besides trivia, what are your other hobbies and interests?
Derek: I’m a huge fan of Pittsburgh’s sports teams, especially the Pittsburgh Steelers and the University of Pittsburgh. I was a four-year trombonist for the Pitt marching band and still occasionally perform at their Alumni Band Day for homecoming. I’m also a huge fan of puzzles and crosswords, and I’ve recently tried writing some crossword puzzles of my own.
Tim: If you could have dinner and play trivia with any five guests in history, who would you choose?
Derek: 1.) Ken Jennings. He’d obviously have the trivia part down, and he’s one of my personal heroes.
His run on Jeopardy! convinced me that being smart can be cool and even financially rewarding.
I’d love to talk to him about his 74-game winning streak and get some pointers on how to be a
better quizzer.
2.) Abraham Lincoln. He was my favorite president as a kid and my parents often jokingly said that I
look like him. I’d like to ask about his decisions during the Civil War and his plans for healing the
nation had he not been assassinated.
3.) Barack Obama. Obviously an expert on American history and government, but he’d also be great
on sports questions. I’d be interested in asking about his presidency, his thought processes
behind major events in it, and his thoughts on our current political discourse.
4.) David Bowie. One of the most intellectually curious artists in music history, and modern music
would be much different without his influence. He was a music expert, but he was also very well-
read and often discussed topics like history, literature, and philosophy. I think he would have
made a great bar trivia player.
5.) William Shakespeare: I’d ask about his creative process, and his wordplay and puns would
probably make him very popular at the table. He’d probably also ace questions about history and
ancient literature, since his plays often mention them.
Tim: What films did you watch in 2026 and which of them should win Oscars?
Derek: To be honest, I don’t really keep up with recent movies as much as some other people. I’d have toimagine that The Odyssey and Christopher Nolan are likely the frontrunners for Best Picture and BestDirector, but anything can happen.
Tim: What is your favorite food and beverage? What is the dining scene like in your city?
Derek: I’m a fan of Primanti Brothers (a local chain that famously serves French fries on its sandwiches). I’vetried every sandwich on the menu at least once, and my personal favorite is the Pastrami and Cheese at the original Strip District location. Pro tip: order it with a side of spicy beer mustard. As for beverage, Pittsburgh is a great city for craft beer. We have a lot of breweries here. Some personal favorites are Dancing Gnome (home to Drew’s Clues Trivia with Sarah on Wednesdays, where I’m a semi-regular), Hitchhiker (the Mt. Lebanon location hosts Buzz Worthy Pub Trivia on Wednesdays), Hop Farm (home to Madcap Trivia on the first and third Monday of the month), and Church Brew Works (the building used to be a Catholic church, and they lean heavily into that theme).
Tim: What are the top international destinations you would choose to visit?
Derek: The only time I’ve traveled outside the U.S. was a trip to Toronto in 2011 with the Pitt marching band. I had fun, so I certainly wouldn’t mind going back. The other cities I’ve thought about are London and Tokyo. London has a lot of history, a lot of free museums, and a lot of great tourist attractions. Tokyo has a vibrant atmosphere and great public transit, so maybe I could even take a bullet train to see other parts of Japan.
Tim: Thanks for chatting. I wish you good fortune in the quizzes to come.
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