It doesnt really fall into the worst time category but I played Talisman last weekend with my daughter and it was quite funny as she wanted the game to be as hard as possible so we played only Cataclysm + base adventure deck + Firelands + Harbinger and a hidden ending. The game went on and looked quite hopeless for both of us. The 6th omen (Rise of the dead prophecy) was on and each of us had already buried three characters, the board was spread all over with firelands token and we didnt stand a chance getting stronger to enter the Inner region. Then all of a sudden I drew three Harbinger cards and it was The Apocrypha (if the last omen gets discarded you get to win the game instead of everyone losing) and two altars (pay 1 life, it does something and the actual omen gets discarded). I had 5 lives at the time so I lost 4 lives in a row (2 from the altars and 2 from the apocrypha) and won the game instantly to my daugters dismay:)

I had never thought I could get to try the Apocrypha because its almost impossible to get the 7th omen discarded (the Harbinger expansion doesnt really make the game that harder), the Firelands adventure deck on the other hand mixed with only the base adventure deck makes the game almost unwinnable, I mean really try it, its quite fun.