Here’s a little rundown of one of the best romantic comedies of all time.
THINGS I LOVE
1. Billy Crystal. A seemingly unlikely romantic leading man, Crystal completely nails Harry’s dry wit, cynical outlook, and jaded vulnerability. The only time he came close to being this adorable was when he starred in the seventies-era TV spoof “Soap.” Harry is how I’ll see Billy Crystal forever.
2. Meg Ryan. Ryan’s sweet and natural and perfect in the role of Sally. In my opinion, Sally is Meg Ryan’s signature role. It’s why people fell in love with her…and fall back in love with her every time they watch it.
3. New York. Any movie set in New York has an unfair advantage, but this one shows The Big Apple in both fall and winter. This means we get to see New York in all its holiday season glory: bright orange leaves, Christmas trees being dragged down snowy sidewalks, New Year’s Eve parties with fabulous people. Score. A direct hit.
4. The soundtrack. Harry Connick, Jr’s renditions of “It Had to be You,” “Where or When,” and “I Could Write a Book” are perfect.
5. The writing. Norah Ephron knocked it out of the park. The repartee between Harry and Sally is fantastically smart and funny.
The phrase “high maintenance” and came from this film.
6. Meg Ryan’s clothes. Classic with a hint of prep, Ryan’s clothes sum up everything I always loved about fall clothes growing up: chunky sweaters, blazers, cute hats, spiffy boots, gloves. It amazes me that although the movie was released in 1989, there’s hardly a trace of bad eighties fashion anywhere in the movie.
7. Aqua Net. The scene in Sally’s car when Harry and Sally are driving from Chicago to New York after college and they stop for dinner late at night, then Sally sprays down her Farrah hair with Aqua Net before getting out of the car will always be one of my favorite parts of the movie.
LINES I LOVE
(in no particular order)
“Someone is staring at you in “Personal Growth.”
“Emily is AUNT Emily?”
“Repeat after me. Pepper.”
“Pepper.”
“Pepper.”
“Pepper.”
(laughs)
“Waiter, there is too much pepper on my paprikash.”
“Waiter (laughs) there is too much pepper on my paprikash.”
“But I would be proud to partake of your pecan pie.”
“Pecan piiie.”
“Pecan piiie.”
“You take someone to the airport, its clearly the beginning of the relationship. And that is why I have never taken anyone to the airport at the beginning of a relationship.”
“Why?”
“Because eventually things move on and you don’t take someone to the airport and I never wanted anyone to say to me, How come you never take me to the airport anymore?”
“Its amazing. You look like a normal person but actually you are the angel of death.”
“I’m Ben Smalls. Of the Coney Island Smalls.”
“And right then I knew. I knew the way you know about a good melon.”
“Well, let’s just say I’m not a big fan of Jimmy Breslin.”
“Well, he’s the reason I became I writer, but that’s not important.”
“See, that’s your problem. Somewhere between fifteen minutes and all night is your problem.”
“I don’t HAVE a problem.”
“Yeah, you do.”
“How much worse can it get than finishing dinner, having him reach over, pull a hair out of my head, and start flossing with it at the table?”
“Oh! I’ve been looking for a red suede pump!”
“You know, I’m so glad I never got involved with you. I just would have ended up being some woman you had to get up out of bed and leave at 3:00 in the morning and go clean your andirons, and you don’t even have a fireplace, not that I would know this.”
“I want you to know…that I will never want that wagon wheel coffee table.”
“Oh, but Baby Fish Mouth is sweeping the nation.’
“I’ll have what she’s having.”
TRIVIA
Did you know the deli scene was Meg Ryan’s idea?
And did you know “I’ll have what she’s having” was Billy Crystal’s idea?
And did you know the lady who utters that line is Rob Reiner’s mother?
And did you know the character of Harry is based on Rob Reiner’s experiences with dating following his real-life divorce?
And did you know the character of Sally is an amalgam of Norah Ephron and her friends?
And did you know the role of Sally was almost given to Molly Ringwald?
And did you know Albert Brooks turned down the role of Harry?
And did you know the role of “Aunt Emily” was played by Penny Marshall’s daughter?
TRIVIA QUESTION
For fun, test your “When Harry Met Sally…” knowledge with this question! If you can answer this, you’re a true Harry and Sally fan.
Sally was a journalist. What was Harry’s job?
Ree Drummond is the founder of The Pioneer Woman and a lover of butter, basset hounds and life on the ranch! Ree started her blog in 2006, and now millions visit ThePioneerWoman.com every month for her trusted recipes and fun family stories. Here’s what she has been up to since it all began:
New York Times Bestselling Author
Ree has written two memoirs (Black Heels to Tractor Wheels, and Frontier Follies) plus nine bestselling cookbooks:
The Pioneer Woman Cooks: Recipes from an Accidental Country Girl (2009)
The Pioneer Woman Cooks: Food from My Frontier (2012)
The Pioneer Woman Cooks: A Year of Holidays (2013)
The Pioneer Woman Cooks: Dinnertime (2015)
The Pioneer Woman Cooks: Come and Get It! (2017)
The Pioneer Woman Cooks: The New Frontier (2019)
The Pioneer Woman Cooks: Super Easy (2021)
The Pioneer Woman Cooks: Dinner’s Ready! (2023)
The Pioneer Woman Cooks: The Essential Recipes (2025)
Food Network Host
Since 2011, Ree has been sharing simple, family-friendly recipes—and the occasional kitchen prank!—on her award-winning show The Pioneer Woman, filmed right on Drummond Ranch. Ree is also a regular judge on Food Network competitions, including Christmas Cookie Challenge.
Founder, The Pioneer Woman Collection
Ree has been creating and selling kitchen and home products at Walmart since 2015 and she’s involved in designing every piece and pattern. The line now includes best-selling appliances (you have to see the floral blender!), plus hundreds of pieces of cookware, tableware, and more. Ree doesn’t like to play favorites but the Agatha print has a special place in her heart.
Restaurant and Hotel Owner
Together with her husband Ladd, Ree has opened several bustling businesses in Pawhuska, Oklahoma, including The Pioneer Woman Mercantile—a bakery, restaurant, and general store that draws visitors from across the country (many come for the biscuits alone!), P-Town Pizza, Charlie’s Ice Cream Shop, and The Boarding House, a charming hotel with eight different rooms decorated by Ree and Ladd.
Media Personality
Ree appears regularly on national TV shows like Today, Good Morning America and more—all while managing to keep flour off her shirt.
Wife, Mom and…Grandma!
Ree’s kids (daughters Alex and Paige and sons Bryce and Todd) are all grown up, and as of December 2024, Ree is the proud grandma of the cutest baby ever, Sofia Scott, born to Alex and her husband Mauricio. Ree still cooks for Ladd (and the kids when they’re home), and she also looks after a few mischievous ranch dogs.
