Jon Hamm as Irwin 'Fletch' Fletcher

Lorenza Izzo as Angela de Grassi

Kyle MacLachlan as Ronald Horan

Roy Wood Jr. as Inspector Morris Monroe

Ayden Mayeri as Griz

Marcia Gay Harden as Countess Sylvia de Grassi

John Slattery as Frank Jaffe

Annie Mumolo as Eve

Lucy Punch as Tatiana Tasserly

John Behlmann as Owen Tasserly

Caitlin Zerra Rose as Laurel Goodwin

Aaron Andrade as Julio

Travis "Taco" Bennett as Breez

Nhumi Threadgill as Sha

Anna Osceola as Larry

Gene Amoroso as Pete Who Does the Jumble

Alli Dowling as Baby Charlie

Omar Ghonim as Hotel Waiter

Owen Burke as Detective #1

Bates Wilder as Detective #2 / Gruff Cop Over Phone

Erica McDermott as Detective #3

Eugene Mirman as Marv, Yacht Club Security Guard

Kenneth Kimmins as The Commodore

Shawn Fitzgibbon as Countess de Grassi's Driver

Daniel Baek as Neighborhood Man

Thomas Ciarametaro as Horan's Guard #1

Levon Panek as Horan's Guard #2

Eli Neslund as Bart Robinson

Wendy Bellevue as EMT

Robert Picardo as Count Clementi Arbogastes De Grassi

Marina Re as Italian Housekeeper

Erion Metani as Home Waiter

Domenico Del Giacco as Italian Detective

Sam Xu as Young Sentinel Employee

Evan Palazzo as Piano / Bandleader

D-Tension as Esteban (uncredited)

Marilyn Swick as Hotel Bar Patron (uncredited)

David Torres Jr. as Detective Boston P.D. (uncredited)

Jon Vellante as Waiter