10) Jackie Chiles
Played by Phil Morris, Jackie Chiles represented all four of the main characters during his time on the show, though he was primarily Kramer’s lawyer. The attorney with a quick temper made us laugh with his impatience over something as small as an unwanted piece of cheese on his sandwich. “Who told you put the cheese on? I didn’t tell you to put the cheese on.” Though he had a good reputation as a lawyer, Chiles never seemed to have any luck while representing the gang, as he failed to get them off the hook for a violation of the Good Samaritan Law, resulting in them going to jail in the final episode. Despite his inability to win cases, it would have been outrageous, egregious, and preposterous for Chiles not to make this list. Here he is with his least favorite client, Kramer.
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