- Radio Hosts - Broadcast radio talk show, DJ and other hosts
- Raico, Ralph - American professor of history
- Raimondo, Justin - Editorial director of Antiwar.com
- Rains, Claude - British-born actor with a long career in Hollywood films
- Rand, Ayn - Objectivist philosopher, novelist
- Rand, Carole Ann - Second president of the Advocates for Self-Government
- Ravenal, Earl C. - Professor emeritus of International Relations at Georgetown University
- Raymond, Eric S. - Open source software advocate, author of The Cathedral and the Bazaar
- Read, Leonard E. - Founder of The Foundation for Economic Education
- Reagan, Ronald - Hollywood actor, fortieth President of the United States
- Reed, Lawrence - President of the Foundation for Economic Education, President Emeritus of the Mackinac Center for Public Policy
- Reese, Charley - American journalist, syndicated columnist
- Reisman, George - Professor of economics, author of Capitalism: A Treatise on Economics
- Ricardo, David - 18th/19th century British economist
- Rich, Andrea Millen - Former owner of Laissez Faire Books
- Richman, Sheldon - Editor of the Foundation for Economic Education's The Freeman: Ideas on Liberty
- Riggenbach, Jeff - Journalist, broadcaster, columnist, former executive editor of The Libertarian Review
- Ringer, Robert - Best selling author (Winning Through Intimidation, Looking Out for #1)
- Rivers, Reggie - Denver Broncos running back
- Robbins, Lionel C. - 20th century British economist
- Robertson, Oscar - The "Big O", Basketball Hall of Famer, head of NBA Players Union 1965-74
- Roberts, Paul Craig - Economist, columnist
- Rockwell, Llewellyn H., Jr. - President of the Ludwig von Mises Institute and editor of LewRockwell.com
- Rodgers, T. J. - Co-founder and CEO of Cypress Semiconductor Corp.
- Rodman, Dennis - Professional basketball player, NBA leader in rebounds for seven consecutive seasons
- Rogers, Jim - Founder with George Soros of the Quantum Fund
- Rohrabacher, Dana - Republican congressman from California
- Roosevelt, Franklin Delano - Thirty-second President of the United States
- Root, Wayne Allyn - Sports handicapper, co-founder, chairman and CEO of GWIN Inc.
- Ropke, Wilhelm - 20th century German economist
- Rosemond, John - American family psychologist and syndicated columnist
- Rosenbaum, Alissa Zinovievna@ - Birth name of philosopher Ayn Rand
- Rosenthal, Daniel M. - Investment author, editor of the Silver & Gold Report
- Rossetto, Louis - Founder and past publisher of Wired magazine
- Rothbard, Murray N. - Austrian School economist, author of For a New Liberty: The Libertarian Manifesto
- Royal, Lauren - American historical romance novelist
- Rueff, Jacques - 20th century French economist
- Ruprecht, David - Host of the "Supermarket Sweep" game show
- Russell, Kurt - Film actor, played Snake Plissken in the Escape From New York/L.A. movies
- Russo, Aaron - Oscar winning producer, 2004 Libertarian Presidential aspirant
- Ruwart, Mary J. - Pharmaceutical research scientist, author of Healing Our World, 2008 LP presidential aspirant
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