The term Charlie Sheen used during an interview. Used to express your content for a current situation or lifestyle.
I just landed a new job and I finally had sex with Cindy... winning
by Eric with a K March 12, 2011
A term, made popular by Charlie Sheen, used to describe succeeding in one's own world.
Person A: Hey man, what did you do today?

Person B: Well, I woke up, forgot to feed my dog, found out I'm back on my credit card bills, failed two tests at school and then I got pulled over for having weed. But I got laid by two chicks!

Person A: Wow, how you feeling?

Person B: Duh! Winning!
by Winning2.5 March 10, 2011
The state of constantly destroying every obstacle in front of you. To be a step ahead of and above everyone else.
The only thing I'm addicted to right now is winning.
by Matttttttttttttttfbfbdfb March 3, 2011
High on cocaine or other some other stimulant; popularized by celebrity Charlie Sheen.
1) I just drank three 5 hour energies - I am winning as hell!

2) Yo, let's get winning tonight!
by hum27 March 2, 2011