He was born and raised in Toronto, Ontario. His father, Michael Barry Sr., was a racer himself in England in the 1950s, who until 2006 ran a specialty bike store and manufactured a line of hand-made bicycle frames under his own Mariposa brand. As a result, the younger Barry grew up in a cycling-intense environment, and started racing at a very young age. He has been a professional since 1998. He has spent many years on the Canadian National Team during the early years of his career. His wife is 2004 Olympic Silver Medalist Dede Demet Barry. They have 2 children. Previous to riding for UCI ProTour team Barry spent several years with the team. He also raced with the Saturn Cycling Team for a number of years before going to US Postal Service/Discovery. Barry has raced in 5 Vuelta a Españas and 5 Giro d'Italias but in 2007 had to abandon the Giro due to health issues, which put him out most of the season. He also had to pull out of the 2002 Vuelta a España after colliding with a motorcycle on the eight stage. In 2005 he wrote the book: Inside the Postal Bus, about his experiences at and the 2004 season whilst riding in support of Lance Armstrong. The work contains texts authored by some of his team mates, including George Hincapie. When the doping topic arises in the book, Barry vehemently denies having ever witnessed any drug intake in the team. He and his wife also wrote a training book. He also writes diary entries during his cycling season. His third book, Le Metier, detailing the life of a cycling domestique, was published in 2010 by Rouleur. He is generally considered a support rider, or domestique, helping the team leaders win races, but he will often get the opportunity to go for personal results. He is usually the team leader for Canada for the World Championships. His strengths lie in the time-trial, and hilly road races. He can be counted on for grand tours, and other stage races as well. For 2010, he left, and signed with for 2 years. On 24 June 2010, Team Sky announced that Barry would be part of its 2010 Tour de France team. This would be Barry's first Tour de France appearance after thirteen seasons as a professional. On 5 September 2012, Barry announced he would retire at the end of the season, after his last race, October's Tour of Beijing.
Doping
On 10 October 2012 it was announced by USADA that he would be suspended for six months for admissions of doping during his time with the US Postal Cycling Team. Later that day a statement was released confirming his acceptance of a six-month ban from 1 September 2012 ending on 1 March 2013 along with a stripping of all race results between 13 May 2003 and 31 July 2006. He confessed that the US Postal team and he were using an extensive amount of performance-enhancing drugs.
At the 2006 Tour of Flanders, Barry went down extremely hard in a crash, suffering severe facial cuts and lacerations and also fracturing some vertebrae.
