Top Definition
When a male masturbates (see jack off) while wearing only a tuxedo top and, optionally, other dinner party accessories (options include: handkerchief, top hat, cigar, etc.).

A play on words on the whiskey brand of the same name.
Roger felt fancy on Friday night, so he decided to give himself a Gentleman Jack.
by Andy Heen-Aerms January 16, 2011

Free Daily Email

Type your email address below to get our free Urban Word of the Day every morning!

Emails are sent from We'll never spam you.