Black Monday

Don Cheadle

Maurice 'Mo' Monroe

Andrew Rannells

Blair Pfaff

Regina Hall

Dawn Darcy

Paul Scheer

Keith Shankar

Michael James Scott

Chad

Eugene Cordero

Ronnie

Casey Wilson

Tiffany 'Tiff' Georgina

Yassir Lester

Yassir X

Ken Marino

Larry Leighman / Larry Leighman / Lenny Leighman / Lenny Leighman

June Diane Raphael

Corkie Harris

Blair Beeken

Junior Trader / Karen

Tuc Watkins

Congressman Roger Harris

Jason Michael Snow

Mike

Deanna Cheng

Pamela

Kadeem Hardison

Spencer

Xosha Roquemore

Connie

Mike Kalinowski

Leighman Brothers Double / Lenny Photo Double

Thomas Barbusca

Werner

Adrienne Wells

Nomi Maldona

Danielle Schneider

Agent Deb Fox

Dannah Feinglass Phirman

Agent Missy Mills

Julie Hagerty

Jackie Georgina

Phil Reeves

Henri Georgina

Dulé Hill

Marcus Duane Wainwright III

Michael Hitchcock

Pastor Newell Swafford

Neil Casey

Alvin Rudnick

Janelle James

Joyce

Mel Fair

Newscaster / TV Anchor

Jen Zaborowski

Bunny Bartles

Kim Cooper

Kayla James

Kurt Braunohler

Ty Daverman

Melissa Stephens

Tosh B'Gosh

Patrick Fabian

Governor Putnam

Sam Asghari

Giancarlo

Greg Bryan

Cop #1 / Security Guard

Jackie Torres

Cleaning Lady / Yolli

Melissa Rauch

Shira

Jayden Maddux

Brad

Derek Cecil

Detective Lester / Private Investigator

Bruce Dern

Rod "The Jammer" Jaminski

Bob Rumnock

Reenactment Jammer / Rod "The Jammer" Jaminski Double

Jake Szczepaniak

Cabana Boy Andrusha

Jimmy Smagula

C.O. Dandleton / Richie

Jack Guzman

Numero Dos

Vanessa Bell Calloway

Ruth

Burl Moseley

Waylon

Mark J.P. Hood

Herbie

Stephanie Nash

Blair's Mom / Emma

Andrew Carrillo

Butler

Robert Glasper

Bruce / Brucie The Engineer

Kirk Fox

Blair's Dad

Todd Sherry

Dr. Gabe Egon

Rory Scovel

Agent Crandall

Chasty Ballesteros

Beautiful Woman

Corey Allen Kotler

Obnoxious Guy #1

Jason Andre Smith

Obnoxious Guy #2

Dan Warner

Sobbing Stock Broker

Dennis Delsing

Old Trader

Hugh Dane

Calvin

Joey Napoli

Random Trader #1

Daniel Strauss

Random Trader #2

Harry Zinn

Random Trader #3

Paul Rust

Brandt

Bob Turton

Kurt Covington

Teresa Ganzel

Trisha

Christine Sclafani

Linda

Tim Russ

Walter

Johnny Williams

Chip

T.J. Hoban

Jackson Polack

John Koyama

Yakuza Member

Jason Boggs

Fat Fred

Iyad Hajjaj

Mujahideen Leader

J Ferguson

Bartender

Tim Heidecker

Not Milken #1

Fred Melamed

Not Milken #2

Fay DeWitt

Rosemarie

Chip Sickler

Delivery Man

Marcy Goldman

Nurse

Jacob Melton

Not Milken #3

Elia Cantu

Suki

Adam Zastrow

Thug #1

Michael Delgado

Thug #2

Derek Graf

Cop #1

Sergio Garcia

Cop #2

Bruce Beatty

Cecil

A.J. Tannen

Agent Durney

Steve Bethers

Homeless Man

Blaine Gray

Leighman Brothers Photo Double

Jim Meskimen

Host of "America's Most Unsolved Crimes"

Kavan Reece

Reenactment Blair

Jennifer K. Lee

Reenactment Dawn

Tim McKernan

Reenactment Keith

Mary-Beth Manning

Roxanne

Artemis Pebdani

Realtor Anna

Monica Garcia Pérez

Maid

Jonathan Stoddard

Cabana Boy Dave

Mark Proksch

Lou "Jewdini" Dinowitz

Bridgid Coulter

Sharon

Jay Santiago

El Sastre

Freddy Bouciegues

Numero Uno

Kevin Gardner

Uncle Hugh

Annie Korzen

Mona

Jazlynn Belle

Little Girl

Joachim Powell

Huey

Shannon McKain

Shady Guy

Mónica López Aleman

Gun-Toting Mom

Jason Chu Wing-Tong

Seary Gordon

Kiralee Hayashi

Big Hair Teller

Arielle Gottesman

High School Girl 1

Jamar Malachi Neighbors

Server

Chelsea Devantez

Linda (Big Fan)

Meredith Thomas

White Lady

Dana Gould

Dennis

Bridger Winegar

Concierge

Michael James Bell

Tailor

Jay Jackson

Barber

Mia Moore

Shontiqua

Helen Wilson

Homeless Lady

Marco Khan

Jimmy

Annie Ellis

Stunt Old Lady

Arielle Reitsma

Beautiful Woman

Anna Maganini

Nanny

Toby Grey

Boy

Irene Roseen

Marina

Josh Shibata

Waiter

George Ketsios

Agent Bergin

Alfred Rubin Thompson

Sam

Jeffrey Markle

Judge Martin

Jen Kober

Lydia

Patrick M.J. Finerty

CEO

Rachel Winfree

Tour Guide

Brick Jackson

Gate Guard

Micah Giovanni

Young Blair

Josh Gilmer

Chris

Jim O'Brien

Bartender

Michael Drake Krueger

JFK JR.

Reagan Gomez-Preston

Parole Officer

Monti Washington

Tony

Rebecca Ann Johnson

Doreen

Zander David Hodgson

Page

Kristen Lapari

Female Employee

Jim McCaffree

Station Manager

Nelson Scott

Melvin

Elizabeth O'Donnell

Adele

Aamina Gant

Server

Terrence Edmonds

Club Kid #1

Jan Munroe

Elder #1

Angel Garet

Hot Jesus

Jacob Berger

Burly Grip

Phil Culotta

Cop

Bronson Pinchot

Douglas 'Doug' Blackmore

Julia Duffy

Maxine Blackmore

Skyh Alvester Black

Arnie Markowitz

Tre Hall

Rasheed

Tony Winters

Robert Ellis

Francisco Rodriguez

Rolando

Johnny Skourtis

Photographer

Jason Medwin

Security Guard

Alan Heitz

Stage Manager

Delilah Day

Prostitute #1

Jessica Ryan

Prostitute #2

Brad Newman

Doug - Stunt Double

Allen Waiserman

Drag Tiff

Aaron Stanford

Doctor

John Lavelle

Gene

Caleb Williams

Kid #1

Orson Ford

Kid #2