I was drawn back to a rewatch of this following hearing Lucy Prebble on the ALWAYS EXCELLENT Rule of Three podcast – and though visibly an artefact of its time, I thought it was an incredibly well put together film. Romantic comedy masterclass, and makes me smile to see Billy Crystal as a romantic lead (albeit something of an asshole, for the most part). 
During their travel from Chicago to New York, Harry and Sally debate whether or not sex ruins a friendship between a man and a woman. Eleven years later, and they're still no closer to finding the answer.
Production countries: United States of America
Production companies: Castle Rock Entertainment, Nelson Entertainment
- Billy Crystal
- Role: Harry Burns
- Meg Ryan
- Role: Sally Albright
- Lisa Jane Persky
- Role: Alice
- Michelle Nicastro
- Role: Amanda
- Gretchen Palmer
- Role: Stewardess
- Robert Alan Beuth
- Role: Man on Aisle
- David Burdick
- Role: 9 Year Old Boy
- Harley Jane Kozak
- Role: Helen
- Joseph Hunt
- Role: Waiter at Wedding
- Kyle T. Heffner
- Role: Gary
- Kimberley LaMarque
- Role: Waitress
- Stacey Katzin
- Role: Hostess
- Estelle Reiner
- Role: Older Woman Customer
- John Arceri
- Role: Christmas Tree Salesman
- Peter Day
- Role: Joke Teller at Wedding
- Kuno Sponholz
- Role: Documentary Couple
- Connie Sawyer
- Role: Documentary Couple
- Charles Dugan
- Role: Documentary Couple
- Katherine Squire
- Role: Documentary Couple
- Al Christy
- Role: Documentary Couple
- Frances Chaney
- Role: Documentary Couple
- Bernie Hern
- Role: Documentary Couple
- Rose Wright
- Role: Documentary Couple
- Aldo Rossi
- Role: Documentary Couple
- Dona Hardy
- Role: Documentary Couple
- Peter Pan
- Role: Documentary Couple
- Jane Chung
- Role: Documentary Couple
- Bob Ader
- Role: Tap Dancer (uncredited)
- Nicholas Glaeser
- Role: Waiter (uncredited)
- Randy James
- Role: Diner Patron (uncredited)
- Stanley Moore
- Role: Truck Driver (uncredited)
- Larry Sherman
- Role: Dinner (uncredited)
- Marilyn Spanier
- Role: Tap Dancer (uncredited)
- John Speredakos
- Role: New Year's Partygoer (uncredited)
- Terry Vaughan
- Role: Giants Fan (uncredited)
- Anthony Welch
- Role: Restaurant Patron (uncredited)
