Five O. Henry stories, each separate. The primary one from the critics' acclaim was "The Cop and the Anthem". Soapy tells fellow bum Horace that he is going to get arrested so he can spend the winter in a nice jail cell. He fails. He can't even accost a woman; she turns out to be a streetwalker. The other stories are "The Clarion Call", "The Last Leaf", "The Ransom of Red Chief", and "The Gift of the Magi".
Sam "Slick" Brown (segment "The Ransom of Red Chief")
Fred Allen
Joanna Goodwin (segment "The Last Leaf")
Anne Baxter
Della (segment "The Gift of the Magi")
Jeanne Crain
Jim (segment "The Gift of the Magi")
Farley Granger
Soapy (segment "The Cop and the Anthem")
Charles Laughton
William Smith (segment "The Ransom of Red Chief")
Oscar Levant
Streetwalker (segment "The Cop and the Anthem")
Marilyn Monroe
Susan Goodwin (segment "The Last Leaf")
Jean Peters
Behrman (segment "The Last Leaf")
Gregory Ratoff
Barney Woods (segment "The Clarion Call")
Dale Robertson
Horace (segment "The Cop and the Anthem")
David Wayne
Johnny Kernan (segment "The Clarion Call")
Richard Widmark
Joyce Mackenzie
J.B. Dorset (segment "The Ransom of Red Chief")
Lee Aaker
Chief of Detectives (segment "The Clarion Call")
Richard Rober
Mr. Schultz (segment "The Gift of the Magi")
Fred Kelsey
Doctor (segment "The Last Leaf")
Richard Garrick
Narrator
John Steinbeck
Mrs. Dorset (segment "The Ransom of Red Chief") (uncredited)
Kathleen Freeman
Ebeneezer Dorset (segment "The Ransom of Red Chief") (uncredited)
Irving Bacon
Judge (segment "The Cop and the Anthem") (uncredited)
William Vedder
Hotel Desk Clerk (segment "The Clarion Call") (uncredited)
Will Wright
Café Manager (segment "The Cop and the Anthem") (uncredited)
Thomas Browne Henry
Boris Radolf (segment "The Last Leaf") (uncredited)
Steven Geray
Druggist (segment "The Last Leaf") (uncredited)
Warren Stevens
Yokel (segment "The Ransom of Red Chief") (uncredited)
Robert Easton
Jimmy Valentine (segment "Prologue") (uncredited)
Carl Betz
Poker Player (segment "The Clarion Call") (uncredited)
Herb Vigran
A.J. Crump (segment "The Gift of the Magi") (uncredited)
Harry Hayden
Maurice (segment "The Gift of the Magi") (uncredited)
Fritz Feld
Menkie (segment "The Gift of the Magi") (uncredited)
Sig Ruman
Butcher (segment "The Gift of the Magi") (uncredited)
Frank Jaquet
Dave Bascom (segment "The Clarion Call") (uncredited)
House Peters
Street Extra/Roominghouse Extra/Office Worker at Crump's
Bert Stevens
Cashier (segment "The Cop and the Anthem") (uncredited)
Marjorie Holliday
Irish Cop (Prologue) (uncredited)
Pat Flaherty
Cop (segment "The Cop and the Anthem") (uncredited)
Robert Foulk
Desk Clerk (segment "The Clarion Call") (uncredited)
Everett Glass
Yokel (segment "The Ransom of Red Chief") (uncredited)
Norman Leavitt
Cop (segment "The Cop and the Anthem") (uncredited)
Jack Mather
Man Being Booked (segment "The Clarion Call") (uncredited)
Frank Mills
Mrs. O'Brien (segment "The Last Leaf") (uncredited)
Martha Wentworth
Girl (segment "The Clarion Call") (uncredited)
Ava Norring
Ellie Mae (segment "The Ransom of Red Chief") (uncredited)
Gloria Gordon
Poker Player (segment "The Clarion Call") (uncredited)
A. Cameron Grant
Cop (segment "The Cop and the Anthem") (uncredited)
Tom Greenway
Manager (segment "The Cop and the Anthem") (uncredited)
Thomas Browne Henry
Sheldon Sidney (segment "The Last Leaf") (uncredited)
Bert Hicks
Bookkeeper (segment "The Gift of the Magi") (uncredited)
Jimmie Horan
Bill (segment "The Gift of the Magi") (uncredited)
Richard Hylton
Headwaiter (segment "The Cop and the Anthem") (uncredited)
Richard Karlan
Secretary (segment "The Last Leaf") (uncredited)
Don Kohler
Yokel (segment "The Ransom of Red Chief") (uncredited)
Ann Kunde
Owner (segment "The Cop and the Anthem") (uncredited)
Nick Lekaj
Cop (segment "The Clarion Call") (uncredited)
David McMahon
O. Henry (Prologue) (uncredited)
Tyler McVey
Storekeeper (segment "The Ransom of Red Chief") (uncredited)
Alfred Mizner
Hotel Clerk (segment "The Clarion Call") (uncredited)
William J. O'Brien
Detective (segment "The Clarion Call") (uncredited)
Stuart Randall
Poker Player (segment "The Clarion Call") (uncredited)
Henry Slate
Street Extra / Roominghouse Extra / Office Worker (uncredited)
Bert Stevens
Bar Customer (segment "The Clarion Call") (uncredited)
Harry Tenbrook
Girl (segment "The Last Leaf") (uncredited)
Beverly Thompson
Umbrella Man (segment "The Cop and the Anthem") (uncredited)
Philip Tonge
Guard (Prologue) (uncredited)
Phil Tully
Waiter (segment "The Cop and the Anthem") (uncredited)
Ernö Verebes
Neighbor (segment "The Last Leaf") (uncredited)
Ruth Warren
Bystander (segment "The Cop and the Anthem") (uncredited)
Billy Wayne
Manager (segment "The Clarion Call") (uncredited)
Will Wright
Mother (Prologue) (uncredited)
May Wynn
Pete (segment "The Gift of the Magi") (uncredited)
Richard Allan
Convict (Prologue) (uncredited)
Phil Arnold
Cisco Kid ((Prologue) (archive footage)) (uncredited)
Warner Baxter
Jimmie Valentine (Prologue) (uncredited)
Carl Betz
Cop in Park (segment "The Cop and the Anthem") (uncredited)
Harry Carter
Yokel (segment "The Ransom of Red Chief") (uncredited)
Robert Cherry
Barney (segment "The Clarion Call") (uncredited)
Abe Dinovitch
Cop (segment "The Cop and the Anthem") (uncredited)
James Flavin