In 1971, Remy was drafted in the 8th round by the California Angels. He played three seasons for the Angels starting in 1975 before being traded to the Boston Red Sox, where he played seven more years. He was an All-Star selection in 1978, though he did not appear in the game. He was released by the Red Sox in 1985. Bill James in his Historical Abstract rated him as the 100th greatest second baseman of all time, as of 2002.

Remy is currently enjoying success in broadcasting, working for the New England Sports Network (NESN), and is the color commentator for all NESN Red Sox broadcasts along with play-by-play announcer Don Orsillo. He is a well-loved figure in Red Sox Nation, bringing his humble yet affable personality to every televised game. Small traditions followed by Jerry include always greeting Spanish-speaking viewers with Buenas noches amigos or another appropriate greeting upon the announcement of the SAP simulcast, and by bringing a doll of Wally the Green Monster (the Sox' mascot) and his white adirondack chair to the announcer's booth of every ballpark the Red Sox visit. Remy loves to regale viewers with tales of his frequent vacations in Aruba. He is affectionately known as the "Rem Dawg". He lends this nickname to his hot dog stand, "RemDawgs" on Yawkey Way outside of Fenway Park in Boston on game days. He is planning to open a second location at Boston's Logan Airport. He also runs a web site, The Remy Report, and is the author of the book Watching Baseball.

Remy has also served as a color analyst for FOX's national coverage of Major League Baseball, primarily assigned to games in the Northeastern U.S.

Remy will be inducted into the Boston Red Sox Hall of Fame in 2006.