Ryan was a member of the Sheldon-Williams team that defeated the Evan Hardy Souls 41–7 to capture the 1999 Saskatchewan High School provincial championship.

Ryan and Evan Hardy running back Jeff Piercy would both go on to play in the CFL in the years following that game.

[3] During his second season with the Rams, he caught a 109-yard touchdown pass, and led the team in receiving, in addition to his kicking duties.

[11] On September 30, 2007, against the Minnesota Vikings he became the first Packers punter to rush for a first down since David Beverly did so against the Houston Oilers on December 14, 1980.

[12] His rush attempt that resulted in a gain of 7 yards came on a fake punt that was originally intended to be a pass, however, he did not hear the coaches call it off at the last minute.

[9] On October 17, in a game against the Chicago Bears, Ryan was hit by Earl Bennett while trying to make a tackle on Devin Hester's 89-yard punt return for a touchdown.

[30] Ryan played in the final game of the 2010 regular season against the St. Louis Rams and landed a punt on the two-yard line on the fly towards the end of the first quarter.

[32] This marked the first time that a team with a losing record (7–9) has made the NFL playoffs as a Division Champion (NFC West).

[41] In the third quarter of the NFC Championship, in which the Seahawks were trailing 16–0, Ryan threw a 19-yard touchdown pass to Garry Gilliam on a fake field goal.

[42][43] The Seahawks ultimately won the NFC Championship by a score of 28–22 and advanced to their second straight Super Bowl.

[54] On August 21, 2018, Ryan signed with the Buffalo Bills, briefly reuniting him with former Seahawks placekicker Stephen Hauschka.

[57] Ryan's booming leg would often flip field position; he also scored 12 rouges on the year, and even completed a pass on a fake punt, but the play was called back by a penalty.

[59] After the CFL canceled the 2020 season due to the COVID-19 pandemic, Ryan chose to opt-out of his contract with the Roughriders on August 25, 2020.

[64][65] Ryan is married to stand-up comedian Sarah Colonna and has appeared on her podcast Off The Rails, with Josh Wolf, numerous times.

In 2015, he tried out for American Ninja Warrior, cheered on by Seahawk teammates Derrick Coleman and Jermaine Kearse.

[68] He and Colonna both appeared on Bar Rescue as one of the recon spies for Black Light District Rock & Roll Lounge.

[69] Ryan became a co-owner of the West Coast League's Portland Pickles in 2017 and of the American Association of Professional Baseball's Cleburne Railroaders in 2021.