Irwin M. 'Fletch' Fletcher

Jon Hamm

Ronald Horan

Kyle MacLachlan

Angela De Grassi

Lorenza Izzo

Countess Sylvia Di Grassi

Marcia Gay Harden

Inspector Morris Monroe

Roy Wood Jr.

Frank Jaffe

John Slattery

Eve

Annie Mumolo

Griz

Ayden Mayeri

Larry

Anna Osceola

The Commodore

Kenneth Kimmins

Count Clementi Arbogastes De Grassi

Robert Picardo

Tatiana Tasserly

Lucy Punch

Marv, Yacht Club Security Guard

Eugene Mirman

Owen Tasserly

John Behlmann

Laurel Goodwin

Caitlin Zerra Rose

Detective #3

Erica McDermott

Julio

Aaron Andrade

Breez

Travis "Taco" Bennett

Detective #1

Owen Burke

Detective Boston P.D.

Noel Ramos

Sha

Nhumi Threadgill

Horan Private Security #2

Levon Panek

Restaurant patron

Heidi Garza

Pete Who Does the Jumble

Gene Amoroso

Baby Charlie

Alli Dowling

Hotel Bar Patron (uncredited)

Marilyn Swick

Hotel Waiter

Omar Ghonim

Detective Boston P.D. (uncredited)

David Torres Jr.

Countess de Grassi's Driver

Shawn Fitzgibbon

Detective #2 / Gruff Cop Over Phone

Bates Wilder

Neighborhood Man

Daniel Baek

Horan's Guard #1

Thomas Ciarametaro

Hotel Bar/Restaurant Patron

Liz Cameron

Bart Robinson

Eli Neslund

EMT

Wendy Bellevue

Waitress

Sarah Ismail

Italian Housekeeper

Marina Re

Home Waiter

Erion Metani

Sandy Cove Police Officer

Jeff Bouffard

Italian Detective

Domenico Del Giacco

Young Sentinel Employee

Sam Xu

Piano / Bandleader

Evan Palazzo

Esteban (uncredited)

D-Tension

Waiter

Jon Vellante

Bus Driver

Justin Thibault