Edmund Hillary

Andrew Munro

Herself

Hillary Rodham Clinton

Amy Usherwood

Self - 42nd President of the United States

Bill Clinton

Self

Chelsea Clinton

George Lowe

Dean O'Gorman

Herself (Archival Footage)

Phylis Schlafly

Kelson Henderson

Himself

Barack Obama

Alison Bruce

Self

Bernie Sanders

Nick Blake

Self - Correspondent, NBC News

Andrea Mitchell

Stephen Lovatt

Herself (Archival Footage)

Gloria Steinem

Peter Daube

Herself

Marian Wright Edelman

Mick Rose

Herself (Archival Footage)

Kate McKinnon

Himself (Archival Footage)

Jerry Brown

Jared Turner

Himself (Archival Footage)

Pat Buchanan

Ryan O'Kane

Self - Vice Chairwoman, Clinton Campaign

Huma Abedin*

Himself (Archival Footage)

Vince Foster

Self - Reporter, The New York Times

Amy Chozick

Himself (Archival Footage)

Donald Trump

Self - Communications Director, Clinton Campaign

Jennifer Palmieri

Himself (Archival Footage)

Chris Matthews

Himself (Archival Footage)

John McCain

Herself (Archival Footage)

Elizabeth Warren

Self - Former Congressman, Massachusetts

Barney Frank

Self - Press Secretary to the First Lady

Lisa Caputo

Self - Special Assistant to the First Lady

Capricia Penavic Marshall

Self - Arkansas Friend

Ann Henry

Self - Media Consultant, 1992 Clinton Campaign

Mandy Grunwald

Self - Classmate, Yale Law School

Nancy Gertner

Self - Former Senator, Maryland

Barbara Mikulski

Self - Senior Advisor, Clinton Campaign

Minyon Moore

Self - Reporter, Bloomberg

Margaret Talev

Self - Campaign Manager, Clinton Campaign

Robby Mook

Self - Counselor to the President, Clinton Administration

David Gergen

Self - Former Senate Majority Leader

Bill Frist

Self - Journalist, The American Spectator 1992 - 1997

David Brock

Self - Chief of Staff, Clinton Administration

John Podesta