Cunningham was the Eagles second-round pick in
1985 NFL Draft. Randall was also being sought by the
USFL's Tampa Bay Bandits that same year. But then Eagles owner
Norman Braman refused to negotiate with Randall if he accepted offers from the Bandits, but the USFL folded before that would become an issue. In his rookie season he played sparingly as a backup to veteran
Ron Jaworski but made a big splash with his uncanny scrambling ability, though he completed just 34 percent of his passes and threw just one touchdown against eight interceptions. In 1986, new head coach
Buddy Ryan arrived in Philadelphia and made wholesale changes, many of them unorthodox. At the quarterback position, Ryan designated 35-year-old Ron Jaworski the starter but would replace the aging veteran with the fleet-footed Cunningham in third-and-long situations where the youngster’s scrambling would presumably put the defense on its heels. After a hand injury to Jaworski in week 10, Cunningham would replace him as the Eagles’ starter. Cunningham was permanently handed the Eagles' starting job for the 1987 season. Cunningham was said to have reached "elite" status during the 1988 season, when he threw for 407 yards during the "
Fog Bowl" playoff game against the
Chicago Bears.
Cunningham would occasionally exhibit sensational feats of athleticism, perhaps most notably in a 1988 game on
Monday Night Football against the
New York Giants. Linebacker
Carl Banks torpedoed in and crunched the Eagles quarterback at the midriff for a seemingly sure tackle. Cunningham managed to twist his body in midair, put a hand down for balance while parallel to the ground, regain his footing, and pass to tight end
Jimmie Giles for a touchdown. The following season, Cunningham uncorked a 91-yard punt, aided by a strong Meadowlands wind, on third down to clinch a key game against the Giants. The Giants backpedaling defense was unprepared for the punt, allowing it to bounce for more than 24 yards after it traveled 67 yards through the air. As of 2006, it is the fourth-longest punt in NFL history.
Another highlight staple was in a 1990 game against the
Buffalo Bills, when Cunningham, throwing from his end zone, was about to be engulfed from the blind side by
Bruce Smith. Cunningham ducked under the flying tackle and heaved a pass 60 yards into the wind while off-balance on his back foot to wide-receiver
Fred Barnett, resulting in an unforgettable 95-yard touchdown. That same year, Cunningham finished with 942 rushing yards, 3rd most ever for a quarterback, 10th best in the league. This nearly made him the first quarterback to both run and pass for 1,000 yards in a season (which Michael Vick accomplished in 2006). Cunningham also reached another notable milestone: 30 passing touchdowns and 942 yards rushing.