Rutledge was born and raised in Birmingham, Alabama. He was part of a team that earned back-to-back state titles at L. Frazier Banks High School in Birmingham, Alabama. As a senior, he was a member of the 1974 Parade High School All-American team. 
Rutledge played collegiately at Alabama, where he was a member of three SEC Championship teams under Coach Paul "Bear" Bryant. He was the starting quarterback on the 1978 National Championship team. A three-year starter, he also led Alabama to the #2 National ranking in 1977. He also led the Crimson Tide to two Sugar Bowl appearances and two SEC Championships. Rutledge earned MVP honors at the 1978 Sugar Bowl and also earned All-SEC honors in 1978 and 1979.
He finished his college career with a 33-5 record as a starter, which currently ranks him as the University of Alabama's seventh all-time winningest quarterback. He received his degree from Alabama in Business Administration and in 2011, was inducted into the Alabama Sports Hall of Fame.
Rutledge spent most of his career as a back-up QB and a holder on kicks. His finest moment as a professional player came when as a member of the Redskins he came off the bench in a game versus the Detroit Lions in 1990. Trailing 35-14 with 10:37 left in the third quarter Rutledge replaced an ineffective Stan Humphries and led a great comeback. He completed 30 of 42 passes for 363 yards and a touchdown and rushed for 12 yards for the game tying touchdown with only 24 seconds remaining. In overtime, he hit Art Monk with a vital 40-yard pass on third and 15 to help set up Chip Lohmiller's game winning field goal.
That game meant that Rutledge got the nod to start the following week on Monday Night against the Philadelphia Eagles in a game that was to become infamously known as the "Body Bag Game". Rutledge, first, and then Stan Humphries were knocked out of the game, leaving emergency quarterback Brian Mitchell (a kick returner and former college quarterback) to finish the game. Rutledge would never start an NFL game again but he did see spot duty in relief of returning starter Mark Rypien in the Skins 1991 Super Bowl Championship season, including some playing time in the Skins last game of the regular season, again against the Philadelphia Eagles.
In the spring of 2007 Rutledge got his first NFL coaching job when he was hired as quarterbacks coach with the NFL's Arizona Cardinals, with direct charge over Kurt Warner. That year, the Cardinals made a late season run and earned a Super Bowl berth, but lost to the Pittsburgh Steelers, 27-23. When the Cardinals hired a new offensive coordinator at the end of that season, Rutledge and most of the offensive staff were fired.
In April 2010, Rutledge agreed to become the head football coach at Pope John Paul II High School in Hendersonville, Tennessee; where he coached for two seasons, leading the Knights to a 4-18 record. He resigned in the Spring of 2012 to return to Arizona to spend time with his family.  Rutledge led Montgomery Bell Academy to a 41-17 record from 2002-2006, with two state titles in 2002 and 2003 and a #15 ranking in the final USA Today Super 25 poll in 2003.
In May 2013, Rutledge was hired by Valley Christian High School in Chandler, Arizona as a full-time staff member and also to lead the football program.