Me and my brother are debating what season its in. I say season 5 and he says season 7 but I think we are both wrong.

He posed for the nude painting and it got hung up in the reagle beagle

That episode is in season 8.

It's called "Jack Takes Off" i think, and yea, it's from season 8. :)

Yep, it's one of the last episodes. As a matter of fact, the show is the last time we see the Beagle.

As a matter of fact, the show is the last time we see the Beagle.
And it was the first time we saw the bartendar who was in that scene. I wonder why regulars Mike or Jim didn't play that part instead.