- "No one takes on the Mad Angels in this harbor and lives to tell about it. It's the bottom of the sea for you!"
- ―Charlie to Ryo.
Charlie Grant (チャーリー・グラント Chārī Guranto) is one of the leading members of the Mad Angels, being the leader of the bikers among the gang.
Charlie sometimes hangs around on Dobuita Street and is well known among some of the shopkeepers and bikers for his rudeness and showing off on his bike. He rides around recklessly on his bike at night around the New Yokosuka Harbor District and is always causing problems to warehouses by vandalizing them or beating up the security guards. Despite all this, he isn't very strong, so he makes his men do everything or carries a weapon to fight with.
Ryo Hazuki searches for Charlie after learning from the Heartbeats bartender, Yoshifumi Hato that he should about the Chinese cartel that Lan Di is a part of and even has a tattoo on his arm like him.
Once Ryo enters the tattoo parlor in Okayama Heights, and asks the tattoo artist Takashi Takashiro about Charlie, he reveals that he is sleeping behind a curtain. Once Ryo opens the curtain, Charlie grabs a knife and attempts to attack him with it. He manages to dodge his attacks, and grabs his arm demanding to know about the cartel. He resists the temptation, until he violently pulls his arm. He instructs him to wait at the You Arcade at 3 p.m. the next day.
The next day, as Ryo enters Sakuragaoka, a little boy named Xie Gao Wen runs to him crying and says a man with sunglasses took his soccer ball and that he would give it back if he brought him to the construction site. It was in fact Charlie who came for revenge. He orders three of his henchmen to beat him up. After Ryo beats them, Charlie holds Gao Wen hostage and one of his henchmen, Minoru Okayasu, is behind Ryo with a pipe. Gao Wen drops his soccer ball, so then Ryo kicks the ball into Charlie's face and knocks out the man behind him. Charlie runs away and tells him not to think he will get away with this.
Later on, when Ryo is working at the New Yokosuka Harbor District, Charlie returns with some henchmen, riding motorcycles on the night of his fourth day of work. They attempt to run over him (Charlie and/or one other henchman can if one or both of the first two QTE's are failed), and then he jump kicks the third driver and rides his motorcycle to chase the other two throughout the harbor. Once Ryo catches up to Charlie, he orders a bunch of henchmen to throw him at the bottom of the sea. Once he defeats all of them, Charlie faces him in a one-on-one hand-to-hand fight. Ryo ends up becoming the victor and interrogates him as he tries to escape demanding to know how the Mad Angels and Chi You Men are connected. He reveals to him that a "Chinese bigshot" is leaving the harbor soon and that he already arranged a crew and ship for him. He reveals that the bigshot wears a silk robe with a dragon on it, which is Lan Di. He begs him not to tell anyone or they'll kill him.
Charlie does not appear or is mentioned again in the series. It is unknown if he was killed by the Mad Angels if they found out that he gave away the information about Lan Di, so this leaves his status as unknown.
Charlie is known by the people of Dobuita as a "poser", a "loser", and a "nasty piece of work". Noriyuki Tsuruoka, the owner of Jupitor's Jackets describes him as being "ugly as the worst sin". He's a jerk who feels riding a bike makes him look cool, but he's not a real biker. He even tried to pull a food poison act at Junichiro Nemoto of Smiley Flower Shop's restaurant in Yokohama once.
- In the What's Shenmue? demo, Charlie can be seen riding his motorcycle in free quest, unlike the actual game.
- Charlie's zodiac sign is Leo and he has a O blood type.