He has played in the National Hockey League (NHL) for the New Jersey Devils, Phoenix Coyotes, Columbus Blue Jackets, Pittsburgh Penguins, New York Rangers and Minnesota Wild.

He serves as a co-host of "That's Hockey Talk" with Nick Maraldo and Kyle "Gumpy" Cathcart, which comes out of the Pat McAfee Incorporated Studios.

After remaining unsigned while still playing in the Ontario Hockey League (OHL) with the Erie Otters, however, Rupp opted to return to the NHL entry draft and was subsequently selected 76th overall in 2000 by the New Jersey Devils.

He later made his NHL debut January 13, 2003 with the Devils,[1] where he helped the team win the Stanley Cup after scoring the Cup-clinching goal.

[3] After the 2004–05 NHL lockout, Rupp was traded with Jason Chimera and Cale Hulse to the Columbus Blue Jackets in exchange for Geoff Sanderson and Tim Jackman on October 8, 2005.

[10] In addition to NHL Network, Rupp is a co-host of That’s Hockey Talk, of Pat McAfee Inc. alongside Nick Maraldo and Kyle “Gumpy (Gump)” Cathcart.