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Penn Bowl is an annual, typically 2-day (Friday-Saturday) quiz bowl tournament held at UPenn on the third weekend in January. It's usually the biggest independent tournament of the year, attracting 45-60 teams. In recent years, it has been edited by [[Samer Ismail]].
In 2003, [[Dave Letzler '06]] managed to do $1800 worth of damage to a college car when he swerved over black ice on the NY State Thruway on the way to Penn Bowl. On the same trip, in which Williams had an abysmal 2-7 record in the prelims before sweeping their playoff bracket, [[Jenny McElroy '03]]'s purse was stolen, and many things were charge to her credit card. [[David Rosenblum '03]], [[Daniel Klein Evan Bick '06]], and [[Brian Hirshman '06]] also attended.
In 2004, a short-handed team of [[Daniel Klein'06]], Letzler, and Hirshman managed to go 9-2 in a weak prelim bracket before getting taken down by the [[University of Maryland]] and [[Yale]], and then eking out a victory over [[Brandeis University]] on the famous "twin-slit experiment" question. This trip also exposed Letzler and Hirshman to the classic film [[Army of Darkness]].
2005 may be the most infamous Penn Bowl. [[Williams Trivia]] had been scheduled for midnight-8AM slot on the Friday night of Penn Bowl. The original plan was that the team would drive to UPenn, played its Friday evening matches, return to its hotel with some other players, play Trivia all night, then return to play their day matches on no sleep and drive back home. However, tournament problems led to Penn Bowl being restricted to a one-day event with under 20 teams (and also led to possibly the worst set of questions in the tournament's history). The team still drove down the night before, planning to play from the hotel. However, the Internet connection was not all it was promised, and that strategy proved unfeasible. However, as [[Max Gutman '08]] had a friend at UPenn, the team played from her dorm room as Penn15, finishing second. Notably, [[Zachary Thomas '08]] did an Action bonus impression of Howard Dean in a stairwell which attracted the RA, who threatened to kick the team out of the dorm. After Trivia ended, the team went to the tournament, [[Christopher Paci '08]], Klein, Gutman, and Thomas having played all night and being on no sleep. The team of [[David Mathias '08]], Letzler, Klein, and Hirshman came in second in their half of the draw, while [[Brian Munroe '07]], [[Paul Hess '08]], Thomas, Paci, and Gutman only managed 7th in theirs. The former team ended the tournament in 5th. Additionally, a blizzard occurred during the tournament, pouring several feet of snow up and down the East Coast, leading to an eight-hour drive back to Williams, ending at 4AM on Sunday.