Early in the movie Vinny is introduced to Judge Chamberlain. Vinny proceeds to lie about his work history. Instead of practicing for six months, he's claims he has been practicing for sixteen years. The judge then asks Vinny:
"And what was the outcome?"
He ponders for a moment and says:
"Win some, lose some."
The judge is visibly confused/put off by this answer, but to me it makes sense. Surely lawyers don't win or lose every single case they're handed. What sort of answer was the judge expecting to hear? As well, at the end of the movie, the judge is commending Vinny's abilities. He then chuckles to himself "Win some, lose some." like it's a really weird thing to say.
This line has confused me for years!