Worst as in most embarrassing? A laxer once had to drive me home from his house to my dorm freshman year after I stayed in his bed until 230 in the afternoon while his entire team watched Sunday football in their living room. Then I crawled downstairs, he drove me home, and while he was asking me for certain articles of clothing back, I opened the door while the car was in motion and puked up goldfish (real ones - the night before I had been to a frat party called "Band in the Sand" where you got free cans of beer for eating live goldfish out of a baby pool. I bet my mom's real proud of me).
Worst as in terms of hardest to get through? Freshman year lax again, walking barefoot into a Wawa at 930 on a Sunday morning and asking for an address because apparently Checkered Cab of College Park can't locate the only fucking Wawa on Route 1 without a God damn GPS system.
Worst in terms of longest? A two and a half hour train ride from Paris to London after having sat in Paris Nord for 3 hours at 7 in the morning with no cell phone and no iPod and having gotten only 2 hours of sleep. So, so, SO worth it though.
Worst in terms of most "what the fuck"? Hockey dude was living in a hotel after he signed his NHL contract midway through the season. I went and saw him at 3 in the morning. We fooled around and then he passed out and I snuck out at like 630 in the morning. Ringling Brother's was in town performing where his team played, and all the performers were in the hotel lobby in full gear. Clown costumes, gymnasts suits, total full shit. I had a mild to moderate panic attack when I saw the clowns. Circus FAIL.