Charlie O'Rourke was born May 10, 1917 in Montreal, Canada. He attended high school in Malden, MA. Long after "Chuckin' Charlie" O'Rourke had ended his career at Boston College, Eastern experts persisted in proclaiming him "the greatest football player" in the school's history. Skinny at 155 pounds over a 5-10 frame, O'Rourke was one of the most clever tailbacks the game has ever known, bringing a twinkle to the eyes of a young head coach named Frank Leahy.

He lead Boston College to a 9-1 record in the 1939 regular season campaign, and the Eagles' first bowl invitation. BC lost to Clemson, 6-3, in that 1940 Cotton Bowl contest, but the wily triple-threat artist from Malden, Massachusetts would not be denied. He used his senior season to catapult the Eagles to a 10-0-0 record and inspired the Eagles to a come-from-behind 19-13 victory over powerful Tennessee in the Sugar Bowl. However, O'Rourke's finest acclaim came earlier that season; in a classic battle with previously unbeaten Georgetown - a game that Grantland Rice heralded as "the greatest college football game I've ever seen." Boston College was clinging to a 19-16 lead with two minutes remaining when, on fourth down, O'Rourke raced back to his end zone, eluding tacklers for almost a full minute before taking a safety. He then punted BC out of trouble and preserved a 19-18 victory. At Boston College he played one year under Gil Dobie, two years under Frank Leahy, and made All-America in 1940.

He had a pro football career with the Chicago Bears, Los Angeles Dons, and Baltimore Colts in 1942 and from 1946-49. In 1942 with the Chicago Bears, he saw limited playing time behind incumbent starter Sid Luckman. He completed 37 of 88 passes for 951 yards, 11 touchdowns, and 16 interceptions. He also intercepted 3 passes on defense, returned 2 punts, and completed 23 punts for 817 for the 11-0 Bears. In 1946 he joined the Los Angeles Dons of the All-America Football Conference as starting quarterback. In 2 seasons in Los Angeles he completed 194 of 354 passes for 2,699 yards, 25 touchdowns, and 30 interceptions. In 1948 he joined the AAFC's Baltimore Colts as a punter and back up quarterback behind Hall-of-Famer Y.A. Tittle. In 1949 he played only 5 games before retiring and becoming an assistant coach for Baltimore until the team folded in 1950.

He coached football at the University of Massachusetts 1952-59. He served as commissioner of the Pop Warner League, a national organization of junior football teams.