[citation needed] Ryan began playing basketball at John Jay High School, where, as a senior, he averaged 26 ppg.
In his first season in a recreational league at West 4th, Ryan played one game against former Detroit Pistons player Phil Sellers and scored 44 points.
[citation needed] According to an article written by Bobbito Garcia about Ryan in Slam Magazine Streetball Special Collector's Issue, Chris Mullin once described Jack as the best shooter he'd ever seen who hadn't played in the NBA.
"[2] Ryan further proved his mastery of the 3-point shot when he won the 2005 City Slam 3-Point Shooting Championships, which aired on ESPN.
In a close final, Ryan edged out fellow streetball sharpshooter Deshun "Father Time" Jackson to take the title.