Because you like Edward Kenway in Assassin's Creed Series
An opportunistic fugitive-turned-bounty-hunter, Faye Valentine uses both grit and her good looks to get ahead. See them in Cowboy Bebop.
Vash might act like a carefree, peace-loving goof, but it's not wise to underestimate this "Humanoid Typhoon." See them in Trigun.
Kara "Starbuck" Thrace will beat you in cards, drink you under the table, then fly circles around you in her fighter plane. See them in Battlestar Galactica.
Charismatic, sociopathic, and dramatic, Charlie Bronson wants nothing more than to be famous. See them in Bronson.
Roger Kint is a nervous, weak, ham-handed criminal. We think. See them in The Usual Suspects.
Working as a captain in the American Expeditionary Forces and a spy for British Intelligence, Steve Trevor wants to end World War I once and for all. See them in DC Extended Universe.
Terence Fletcher is a brutal and unflinchingly strict music teacher hell-bent on whipping his students into shape. See them in Whiplash.
A stylish agent, Agent J would rather improvise than play by the rules. See them in Men in Black.