- Derek Waters - Himself - Host / Various Characters
- Derek Waters - C.S. Forester
- Zach Gilford - Jim Abbott
- Adrianne Palicki - Kate Warne
- Will Ferrell - Roald Dahl
- Octavia Spencer - Harriet Tubman
- Maestro Harrell - Louis Armstrong
- Andre Royo - King Oliver
- Jason Momoa - Jean Lafitte
- Maya Rudolph - Griselda Blanco
- Josh Hartnett - Clark Gable
- Justin Long - Arno Penzias
- Greg Kinnear - Thaddeus Lowe
- Christopher Meloni - Othniel Marsh
- Mark Proksch - Himself - Storyteller
- Kat Dennings - Kentucky Daisey
- Ellie Kemper - Nellie Bly
- Haley Joel Osment - Kid Blink
- Noah Wyle - Thomas Nast
- Jason Alexander - William Tweed
- Zach Woods - Lee Duncan
- Ryan Phillippe - Benjamin Hayes
- Giancarlo Esposito - Andrés Pico
- Jason Mantzoukas - Pope
- Jesse Plemons - William Kenward
- Jesse Plemons - Edgar Allan Poe
- Patton Oswalt - Mac Brazel
- Thomas Lennon - Major Marcel
- Parker Posey - Mary Phelps Jacob
- Colin Hanks - Fred Rogers
- Colin Hanks - Gordon Cooper
- Colin Hanks - Ernest Thompson Seton
- Henry Winkler - Zenas Fisk Wilber
- Michael McKean - Carl Laemmle
- Sam Rockwell - Bugsy Siegal
- Donald Faison - Joe Louis
- Dennis Quaid - Lucky Luciano
- Nathan Fillion - Wernher von Braun
- Chelsea Peretti - Ann Druyan
- Adam Devine - Pavel Belyayev
- Blake Anderson - Alexey Leonov
- Liev Schreiber - Victor Lustig
- Stephen Merchant - Abraham Lincoln
- Stephen Merchant - F**kin' President Lincoln
- Randall Park - Himself - Storyteller
- Aaron Takahashi - Frank Emi
- Grant Imahara - Frank Inouye
- Jack Black - Vincenzo Peruggia
- Jack Black - Elvis Presley
- Jack Black - William Mulholland
- Rachel Bloom - Herself - Storyteller
- Kimiko Glenn - Maya Lin
- Jenny Slate - Herself - Storyteller
- Jenny Slate - Herself - Narrator
- Jon Gabrus - Himself - Storyteller
- Jennie Pierson - Herself - Storyteller
- Solomon Georgio - Himself - Storyteller
- Shannon Woodward - Ida Tarbell
- David Koechner - John Pastore
- John Ennis - John D. Rockefeller
- David Harbour - Vietnam Memorial Head
- Kyle Mooney - Himself - Storyteller
- Alison Rich - Herself - Storyteller
- Jason Ritter - Art Heist Investigator
- Jason Ritter - Robert Wilson
- Jason Ritter - Stetson Kennedy
- Jason Ritter - Elisha Gray
- Michael Cera - Maurice Cohen
- Michael Cera - John Endicott
- Kirsten Dunst - Agatha Christie
- Jayma Mays - Florence Schaffner
- Vanessa Bayer - Mary Gillespie
- Claudia O'Doherty - Herself - Storyteller
- Steven Weber - Lomax
- Natasha Leggero - Herself - Narrator
- Natasha Leggero - Elizabeth Bisland
- Will Forte - Edwin Booth
- Jonathan Ames - Junius Booth
- Adam Scott - John Wilkes Booth
- Dave Grohl - Memphis Mafia Member
- Fred Willard - Deep Throat
- Kyle Kinane - Self - Narrator
- Joe Lo Truglio - Al Capone
- Matt Besser - Edwin Stanton
- Ike Barinholtz - August Spies
- Charlie Finn - Cpt. 'Black Jack' Bonfield
- Eric Filipkowski - Abraham Lincoln
- Will Sasso - Frank Nitti
- Moshe Kasher - Albert Parsons
- James Atkinson - Himself - Narrator
- Johnny Knoxville - Marshall Ratliff
- Johnny Knoxville - Ponce De Leon
- Johnny Knoxville - Johnny Cash
- Bill Hader - John Pemberton
- Simon Helberg - Frank M. Robinson
- Rob Riggle - J. Edgar Hoover
- Rob Huebel - Governor Trevino
- Rob Huebel - Pat Garrett
- Bob Odenkirk - Richard Nixon
- Bob Odenkirk - The Guy
- Jack McBrayer - Clarence Darrow
- Jack McBrayer - H.R. Haldeman
- Jack McBrayer - Alan Freed
- Jack McBrayer - General Andrew Jackson
- Lamorne Morris - Martin Luther King Jr.
- Kevin Nealon - The Grand Dragon
- Jen Kirkman - Herself - Narrator
- Chris Romano - Himself - Narrator
- Richard Riehle - James Roche
- Richard Riehle - Ralph Himmelsbach
- Chris Parnell - Jim Bowie
- Chris Parnell - Thomas Edison
- Chris Parnell - King Charles II
- Winona Ryder - Mary Dyer
- Ken Marino - Masterpiece
- Ken Marino - Harry Houdini
- Martin Starr - Art Thief
- Jaleel White - Bass Reeves
- Jaleel White - Grandmaster Caz
- June Diane Raphael - Isabella Stewart Gardner
- Alia Shawkat - Alexander Hamilton
- Alia Shawkat - Virginia Hall
- Connie Britton - Patricia Shaheen
- Paul Scheer - Carl Sagan
- Paul Scheer - Colonel Henry Ludington
- Nick Offerman - Johnny Cool
- Craig Anstett - Various
- Rich Fulcher - Porter Wagoner
- Rich Fulcher - Self - Narrator
- 'Weird Al' Yankovic - Adolf Hitler
- Aidan Potter - Various
- Zachary Burke - Various
- Clint Culp - Policeman
- Steve Berg - Various
- Benjamin Poe - Policeman
- Kaci Beeler - Herself - Interviewee
- Artemis Pebdani - Herself - Narrator
- Derrick Beckles - Himself - Narrator
- Tony Hale - Edward Cope
- Tony Hale - James Monroe
- Tony Hale - Meriwether Lewis
- Steve Little - Mark Twain
- Ben Hoffman - Newscaster
- Kristen Wiig - Patty Hearst
- Ally Johnson - Herself
- Paco Romane - Himself
- Paget Brewster - Herself - Narrator
- Tommy Blacha - Self - Narrator
- Taran Killam - William Clark
- Taran Killam - D.B. Cooper
- Taran Killam - Frédéric Auguste Bartholdi
- Jason Schwartzman - Ralph Nader
- Owen Wilson - John Harvey Kellogg
- Luke Wilson - Will Keith Kellogg
- Nathan Fielder - Bob Woodward
- Nathan Fielder - John Lennon
- Alfred Molina - Sir Arthur Conan Doyle
- Polly W. LePorte - Kellogg Patient
- BJ Porter - Himself - Narrator
- Alie Ward - Herself - Narrator
- Matt Walsh - Joseph Pulitzer
- Matt Walsh - KKK Member
- Tim Heidecker - Cop
- Tim Heidecker - Max Schmeling
- Kumail Nanjiani - Lakota Chief
- Bradley Whitford - William Jennings Bryan
- Brett Gelman - Joseph Pulitzer
- Brett Gelman - Art Thief
- Casey Wilson - Dolly Parton
- Lisa Bonet - Mary Ellen Pleasant
- Lisa Bonet - Rosa Parks
- Terry Crews - Joe Louis
- Terry Crews - Donald 'Cinque' DeFreeze
- John A. Lorenz - Lakota Indian
- Michael Kearney - Interviewee
- Lacie Madison - Party Guest
- Mark Gagliardi - Himself - Narrator
- Preston Flagg - Himself - Narrator
- Matt Gourley - Himself - Narrator
- Timm Sharp - Billy the Kid
- Andy Daly - Teddy Roosevelt
- Jake Johnson - William B. Travis
- Mike Coleman - Various
- Mike Coleman - Fireman
- Horatio Sanz - Gen. Santa Anna
- Michael Daniel Cassady - Various
- Sarah Burns - Various
- Adam Nee - Various
- Joseph Billingiere - Various
- Raymond Ochoa - Various
- Eric Edelstein - Himself - Narrator
- Eric Edelstein - Museum Guard
- Ricardo Tirado - Various
- Corey Weber - Tim- The Cowboy
- Joseph Zinsman - Soldier
- Mariah Iman Wilson - Claudette Colvin
- Jerry Minor - Edgar Nixon
- Jordan Peele - Percy Julian
- Amber Ruffin - Herself - Narrator
- Allan McLeod - Himself - Narrator
- Aubrey Plaza - Aaron Burr
- Aubrey Plaza - Sacagawea
- Morgan Murphy - Herself - Narrator
- Michael Coleman - Various
- Juno Temple - Sybil Luddington
- Michaela Watkins - Nurse
- Laura Dern - Nellie Bly
- Eric Falconer - Himself - Narrator
- Suzi Barrett - Herself - Narrator
- J.D. Ryznar - Himself - Narrator
- Lauren Lapkus - Normal Woman
- Retta - Sylvia Robinson
- Da'Vone McDonald - Big Bank Hank
- Ron Funches - Herc
- Jon Daly - Kris Kristofferson
- David Wain - Himself - Narrator
- Colton Dunn - Himself - Narrator
- Bennie Arthur - Various
- Maria Blasucci - Various
- Craig Cackowski - Various
- Tymberlee Hill - Various
- Mort Burke - Various
- Sophia Bush - Bonnie Raines
- Jenna Fischer - Katharine Wright
- Dave Foley - Alexis Pulaski
- Ali Ghandour - Prince Aly Khan
- Lin-Manuel Miranda - Himself
- Questlove - Himself
- Christopher Jackson - Himself
- Ben Folds - Self
- Ben Folds - Nathan Cherry
- Tim Baltz - Various
- Alexandra Grey - Marsha P. Johnson
- Trace Lysette - Elizabeth Eden
- Trace Lysette - Sylvia Rivera
- Paul Rust - John Wojtowicz
- Daryl J. Johnson - Narrator
- Daryl J. Johnson - Robert S. Abbott
Thomas Lennon interpreta a Major Marcel en la serie.
Questlove interpreta a Himself en la serie.
Owen Wilson interpreta a John Harvey Kellogg en la serie.
Winona Ryder interpreta a Mary Dyer en la serie.
Alfred Molina hace el papel de Sir Arthur Conan Doyle.
Lisa Bonet interpreta a Rosa Parks en la serie.
Colin Hanks interpreta a Charles Dickens en la serie.
Laura Dern hace el papel de Nellie Bly.
Jason Alexander interpreta a William Tweed en la serie.
Giancarlo Esposito hace el papel de Andrés Pico.
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