Showing my age with this one, but Ollie North blowing the Virginia Senate race in 1994 (aided by a right-leaning independent candidate) against an extremely flawed and unpopular Democrat in the middle of a historic red wave was a sight to behold. There is a very good documentary about this race/his campaign that I'm forgetting the name of, but if any of the kids here want to learn more you should absolutely track it down. It was such a beautiful (and expensive) disaster and a formative race for me as a political professional.
Also, not a Congressional race but the Newark mayoral election between Sharpe James and Cory Booker was pretty incredible (and also produced a pretty great documentary!). I grew up in North Jersey, a friend of mine was a close Sharpe James aide, and this race produced some of the most memorable (for negative reasons) campaign tactics I've ever seen.
Why was Chuck Robb unpopular in 1994? He was super popular as a Governor and won a landslide in his first Senate race
It was back when normal heterosexual sex scandals mattered.
