During his career, Healy played for the Los Angeles Kings, New York Islanders, New York Rangers and the Toronto Maple Leafs. During the 1992–93 season, he helped lead an up-start New York Islander team to the Wales Conference Finals, shocking the two-time defending Stanley Cup Champion Pittsburgh Penguins along the way. In the 1993 off-season, the Islanders lost Healy to the Anaheim Mighty Ducks in the expansion draft. The next day he was claimed by the Tampa Bay Lightning in phase two of the draft. The very same day Healy was traded to the New York Rangers for a third round pick. Healy was a part of the Rangers Stanley Cup winning team in 1993-94, and he played 68 playoff minutes that year. During the 1995–96 season, Healy won both the Rangers Good Guy Award and the Rangers Fan Club Ceil Saidel Award. At the time he won these awards, he was the Rangers' number-one goalie while Mike Richter was injured. After his long playing career he served as hockey colour commentator and analyst, first for the CBC and then for TSN. He also served as the secondary colour commentator for the NHL on TSN and as an ice-level analyst for TSN's regional Toronto Maple Leafs telecasts. At the start of the 2009–10 NHL Season, he moved back to analyzing games for CBC's Hockey Night in Canada before he joined the NHL on Sportsnet crew in 2014. Healy created the Loch Ness Monster" hockey analysis segment for TSN, in which he picked a player (or players) who was supposed to be a key player that night but did not turn out to be (the tagline being that the player is "the monster you hear about but don't see"). Bagpipes can be heard in the background and the chosen player is dubbed "tonight's Nessie". One notable occurrence was the March 29, 2008, broadcast of the Boston Bruins' 4-0 win over the Ottawa Senators, where Healy selected the entire Senators team that night as the "Nessie". The segment's title is a parody of fellow analyst Pierre McGuire's "Monster" segment, which focuses on a player's whose contributions have been particularly effective.Healy was also a colour analyst for the 2007 Casino Rama Curling Skins Game finals on TSN. Healy lives in Ajax, Ontario. He has three daughters (Megan, Rachel, and Bridget) and has been married to his wife, Susie, since 1990. He is also a musician, playing the bagpipes in several bands around the Toronto area. Healy frequently plays the Warrior's Day Parade on the first Saturday of the Canadian National Exhibition. He is very well known in his hometown region of the Eastern GTA (Greater Toronto Area) for his philanthropic efforts and numerous fundraising activities."
