R
- Nicole Raczynski – Female Pro Wrestler known as Nikki Roxx, and Roxxi in TNA Wrestling
- Sumner Redstone – Chairman of the Board and Chief Executive Officer of Viacom
- Kevin P. Reilly, Sr. – former CEO of Lamar Advertising Company in Baton Rouge and former member of the Louisiana House of Representatives
- Arthur E. Reimer – two time Presidential candidate of the Socialist Labor Party of America
- James Remar – Actor, best known for the role of Ajax in The Warriors
- Lee Remick – Film and television actress
- Jerry Remy – MLB Player and Sports Broadcaster
- Patrick Renna – Actor, best known for the role of Ham in The Sandlot
- Frank Renzulli – Writer/Actor
- Paul Revere – Silversmith and American Revolution patriot
- Jonathan Richman – Musician
- Sam Rivers – Jazz Musician
- Alex Rocco – Actor
- Norman Rockwell – Artist
- Jeremy Roenick – NHL player
- Jereme Rogers – Professional Skateboarder
- John Rowe (1715–1787), Boston resident merchant and diarist, original developer of Rowes Wharf
- Nathaniel Ruggles, Former U.S. Representative
- Bill Russell – Professional basketball player and coach and Olympic gold medallist
- Eli Roth – Director/Writer/Producer/Actor
- Blanchard Ryan – Actress
Read more about this topic: List Of Bostonians