Rise to Fame
During a game on January 2, 2001, Theodore became the second goaltender to score a goal and capture a shutout when he attempted to clear the puck from the defensive zone and put the puck into the then empty net, vacated by Islanders goaltender John Vanbiesbrouck. In the following 2001-02 NHL season, Theodore captured the starting goaltender position from Jeff Hackett after a strong performance that helped the Canadiens gain a berth in the playoffs. His regular season play earned him the Vezina Trophy and the Hart Memorial Trophy the same year. In the play-offs his success continued when the Canadiens beat the top ranked Boston Bruins. Theodore became an immediate fan favorite in the city of Montreal. In 2004 he played back-up goalie for Team Canada, and won the World Cup of Hockey Championship. Theodore had another strong season in the 2004 NHL season as he earned a winning record of 33-28-5 and earning 6 shutouts, one shy of his current record. Also that season he participated in the Heritage Classic, the NHL's first ever outdoors hockey game. The game was held at Commonwealth Stadium versus the Edmonton Oilers, a game which Montreal won 4-3.

On December 15, 2004 his father, Ted Nicholas Theodore, and his half-brother pleaded guilty to charges of loansharking and possession of a restricted weapon. In February of 2005, the 71 year old Ted Theodore was given a $30,000 fine, but no jail time.