A couple here:

First was a TLV => EWR => SFO connecting itinerary. TLV => EWR was delayed 2.5 hours, which seemed fine at first b/c I could still make the last flight of that night to SFO. However, the TSA checkpoint was staffed by... 1 person and had to deal with the ~300 mostly connecting passengers from TLV! With 15 minutes before departure I started showing people my boarding pass and cut as far as possible to the front; had to run to the gate where they closed the door behind me.

The other was my fault; I had 4 too many margaritas after an interview at the Frontera Grill in Chicago; hopped on the metro and... passed out right away. Woke up with the train having already turned around; I got off and on a train back to ORD. But at this point I'd only get there 25 minutes before departure for my flight (last of the night); with a Final Exam the next day and a blizzard due to hit ORD that day. United being United; I ran to the departure board to see it had been delayed 1 hour! Managed to even grab Cubano sandwiches at Tortas Frontera on my way out!

Is there a thread like this for worst delays we've ever encountered?