Irwin M. 'Fletch' Fletcher

Jon Hamm

Ronald Horan

Kyle MacLachlan

Countess Sylvia Di Grassi

Marcia Gay Harden

Angela de Grassi

Lorenza Izzo

Inspector Morris Monroe

Roy Wood Jr.

Frank Jaffe

John Slattery

Eve

Annie Mumolo

Angela De Grassi

Lorenza Izzo

Griz

Ayden Mayeri

Larry

Anna Osceola

The Commodore

Kenneth Kimmins

Count Clementi Arbogastes De Grassi

Robert Picardo

Yacht club security

Eugene Mirman

Tatiana Tasserly

Lucy Punch

Owen

John Behlmann

Cast

Erica McDermott

Laurel Goodwin

Caitlin Zerra Rose

Detective

Owen Burke

Julio

Aaron Andrade

Detective Boston P.D.

Noel Ramos

Breez

Travis Bennett

Sha

Nhumi Threadgill

Horan Private Security #2

Levon Panek

Restaurant patron

Heidi Garza

Pete Who Does the Jumble

Gene Amoroso

Hotel Bar Patron

Marilyn Swick

Baby Charlie

Alli Dowling

Detective Boston P.D.

David Torres Jr.

Hotel Waiter

Omar Ghonim

Countess'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

Waitress

Sarah Ismail

EMT

Wendy Bellevue

Italian Housekeeper

Marina Re

Sandy Cove Police Officer

Jeff Bouffard

Home Waiter

Erion Metani

Italian Detective

Domenico Del Giacco

Young Sentinel Employee

Sam Xu

Piano / Bandleader

Evan Palazzo

Waiter

Jon Vellante

Bus Driver

Justin Thibault

Director

Greg Mottola