Note: I only went with ones who recurred for at least a good chunk of a season, and I used George Steinbrenner as a stand-in for all of George's bosses with the Yankees. For more details on why I went in this order:
  1. Mr. Kruger
    Amazingly, only in four episodes. Felt like longer. Had the show introduced him sooner, he'd be held in the esteem he deserves.
  2. George Steinbrenner
    Thank God they never used the scene they filmed with the real Boss.
  3. Mr. Pitt
    The athletic socks scene alone...
  4. J Peterman
    Certainly, the show got longer and more varied use out of him than any of the others. The others just made me laugh more.
  5. Russell Dalrymple
    Bob Balaban has played both the actual Warren Littlefield and his fictional stand-in here.
  6. Mr. Lippman
    Replacement-level boss.