The finest geek minds we could find test their mettle against the Great American Pop Culture Quiz

I have turned a great many basic tasks — ATM withdrawals, elevator rides, hair growth — into competitions. My cockiness is so overwhelming that humiliating losses — wrestling a female volleyball player in front of my entire freshman dorm, appearing on an MTV game show and yelling ”Dennis Hopper” right after someone had incorrectly guessed ”Dennis Hopper” — just make me come back for more.

I am so competitive that my friends have been chosen not for their kindness, generosity, or charisma, but rather for how upset they get when I beat them at stuff. So when EW devised the Great American Pop Culture Quiz, I gathered five of the geekiest people I could find for a 30-minute, No. 2 pencil, editor-proctored nerdfest. My high school friend Art Chung, a question writer for Who Wants to Be a Millionaire, got a 1470 on his SATs and took them again just because I beat him by 10 points. I bring this up not only because it shows how intense Art is but because it allows me to work in the fact that I got a 1480 on my SATs.

I also invited John Sellers, who wrote the books Arcade Fever and PCAT: Preparation for the Pop-Culture Aptitude Test; Josh Tyrangiel, a music critic at TIME to whom I lose bets almost daily, the most pathetic being a somewhat desperate and drunken wager on whether a cocktail waitress at the Bellagio was from Florida; and Lindsay Goldenberg, a 24-year-old entertainment writer at Teen People who used to pen a sex column for and who I thought might distract everyone. Rounding out the test subjects was Marc Bernardin, the editor of this column, whom I wanted to humiliate for taking out all my good jokes every week, including the one about him that originally ended this sentence.

I knew I was in trouble when I saw the questions. I knew I was in much bigger trouble when we went over our answers. I couldn’t name all the Rat Pack members, even though in the version of the test that we took, their names were prominently featured in the picture accompanying the question. I blew a question, which has since been cut, about Leonardo DiCaprio, whom I spent two days interviewing for TIME. The only thing that made me feel better was that for a surprising number of questions, Lindsay answered ”my mom.” Her pockets of knowledge were fascinatingly diverse: She knew what CBGB stands for, but to fill out the Apocalypse Now quote, ”I love the smell of…” she wrote, ”s — – on a hot day.”

The results were not pretty: Art scored 83 points, Marc 73, Josh 71, John 70, me 56, and we’ll protect Lindsay from any more scorn. I had not done this badly on a test since junior high, when my then girlfriend Lori sat there for a half hour while I tried to remove her bra. Everyone had an excuse. John said he hadn’t choked like this since a third-grade spelling bee when he botched the word piano, prompting his classmates to call him pain-o for the rest of the year. Lindsay blamed generational bias and wanted more questions ”about stuff that involves love.” Marc, who is black, kept insisting there was a cultural bias. When confronted with the fact that he missed both the N.W.A and What’s Happening!! questions, he said, ”This test is not set up for black guys who grew up in the suburbs.”