Patrick Grennan as Self - Relative

Denis Nevin as Self - Butler

Ted Kulik as Self - Boston Guide

Barbara Perry as Self - Historian

David Nasaw as Self - Historian

Reece Klein as Self - Public Relations

Larry Tye as Self - Biographer

Ronald Kessler as Self - Journalist

Alan Posener as Self - Biographer

Janice Hudson as Self - Museum Curator

Timothy Meagher as Self - Historian

John F. Kennedy as Self - Politician (archive footage)

Robert F. Kennedy as Self - Politician (archive footage)

Franklin D. Roosevelt as Self - Politician (archive footage)

Joseph P. Kennedy Sr. as Self (archive footage)

Harry S. Truman as Self - Politician (archive footage)

Rosemary Kennedy as Self (archive footage)

Kathleen A. Kennedy as Self (archive footage)

Patricia H. Kennedy as Self (archive footage)

Peter Lawford as Self - Actor (archive footage)

Richard Nixon as Self - Politician (archive footage)

Jacqueline Kennedy as Self (archive footage)

Eunice Kennedy Shriver as Self (archive footage)

Paul VI. as Self (archive footage)

Ronald Reagan as Self - Politician (archive footage)