Jon Hamm

Irwin 'Fletch' Fletcher

Lorenza Izzo

Angela de Grassi

Kyle MacLachlan

Ronald Horan

Roy Wood Jr.

Inspector Morris Monroe

Ayden Mayeri

Griz

Marcia Gay Harden

Countess Sylvia de Grassi

John Slattery

Frank Jaffe

Annie Mumolo

Eve

Lucy Punch

Tatiana Tasserly

John Behlmann

Owen Tasserly

Caitlin Zerra Rose

Laurel Goodwin

Aaron Andrade

Julio

Travis Bennett

Breez

Nhumi Threadgill

Sha

Anna Osceola

Larry

Gene Amoroso

Pete Who Does the Jumble

Alli Dowling

Baby Charlie

Omar Ghonim

Hotel Waiter

Owen Burke

Detective #1

Bates Wilder

Detective #2 / Gruff Cop Over Phone

Erica McDermott

Detective #3

Eugene Mirman

Marv, Yacht Club Security Guard

Kenneth Kimmins

The Commodore

Shawn Fitzgibbon

Countess de Grassi's Driver

Daniel Baek

Neighborhood Man

Thomas Ciarametaro

Horan's Guard #1

Levon Panek

Horan's Guard #2

Eli Neslund

Bart Robinson

Wendy Bellevue

EMT

Robert Picardo

Count Clementi Arbogastes De Grassi

Marina Re

Italian Housekeeper

Erion Metani

Home Waiter

Domenico Del Giacco

Italian Detective

Sam Xu

Young Sentinel Employee

Evan Palazzo

Piano / Bandleader

Ashley Albrizio

Fruit Stand Patron (uncredited)

Domenic Arduino

Italian Cop (uncredited)

Michael Balzano III

Lyft Driver (uncredited)

Jon Vellante

Waiter

Gina Barber

Clambake Guest (uncredited)

Steve Bertorelli

Bus Passenger (uncredited)

Jeff Bouffard

Sandy Cove Police Officer (uncredited)

Liz Cameron

Hotel Bar Restaurant Patron (uncredited)

Cynthia Clancy

Bus Passenger (uncredited)

D-Tension

Esteban (uncredited)

Adam Desautels

Detective (uncredited)

Tierre Diaz

Lyft Driver (uncredited)

Heidi Garza

Restaurant Patron (uncredited)

Ian Dylan Hunt

Boston P.D. (uncredited)

Sarah Ismail

Waitress (uncredited)

Stephen Kyle

Buss Passenger (uncredited)

Marilyn Swick

Hotel Bar Patron (uncredited)

Juan Szilagyi

Fisherman (uncredited)

David Torres Jr.

Detective Boston P.D. (uncredited)