Billy Crystal on ‘When Harry Met Sally,’ ‘Spinal Tap,’ ‘Standing Up, Falling Down,’ and Drinking Jägerbombs

As someone that grew up watching Billy Crystal in the movies and on TV, when I found out that I could talk with him for his recent movie Standing Up, Falling Down, I jumped at the chance. After all, Crystal’s work in The Princess Bride, This is Spinal Tap, SNL, City Slickers, Analyze This, hosting the Oscars and Comic Relief, and too many things to mention were hugely influential on this kid from suburbia. I honestly don’t know how many times I’ve seen The Princess Bride and Spinal Tap but it’s not a healthy number. In addition to his work in front of the camera, he also directed movies like Mr. Saturday Night, 61*, Forget Paris, and the upcoming Here Today with Tiffany Haddish. Like I said, I’ve been a fan a long time.

If you’re not familiar with Standing Up, Falling Down, the film was directed by Matt Ratner and it’s about a struggling Los Angeles stand-up comedian (Ben Schwartz) that moves back home to Long Island and the unlikely friendship that forms with his alcoholic dermatologist (Crystal). While this could easily be some sappy TV movie of the week, the reason this movie works is the great chemistry between Schwartz and Crystal. Each delivers a fantastic performance and it was nice seeing Crystal play a dramatic role where a joke won’t get him off the hook. Definitely recommended. The film also stars Eloise Mumford, Grace Gummer, David Castañeda, Kevin Dunn, and Debra Monk.

Shortly after seeing the film I landed an extended interview with Crystal. During the wide-ranging conversation Crystal shared some fantastic stories about making This is Spinal Tap, When Harry Met Sally, working with Robin Williams (including recreating a late night phone call with the amazing comedian), what drew him to Running Scared and Throw Momma From the Train, how Mr. Saturday Night happened and what it was like to direct and star in the project, what it was like making Standing Up, Falling Down, the status of Pixar’s Monsters at Work for Disney+ with John Goodman, if they ever talked about making another sequel to Analyze This or City Slickers, and so much more.

If you are a Billy Crystal fan I promise you will enjoy this interview. And if you’re a Robin Williams fan, make sure you watch starting at nine minutes and fifty-five seconds.

Check out what he had to say in the player above and below is an exact listing of what we talked about.

Billy Crystal:

• How he recently got the COVID vaccine.
• What TV series would he like to guest star on?
• How he became friends with Rob Reiner on All in the Family.
• What movie has he seen the most?
• Who doesn’t get enough credit behind-the-scenes when you’re making a movie?
• What does he remember about making This is Spinal Tap and did he have any idea it would be such a big hit?
• What was it like working with Robin Williams?
• How they raised 70 million dollars doing Comic Relief.
• 9:55 – He replays a late night call from Robin Williams and what they talked about.
• 11:35 – The status of Pixar’s Monsters at Work with John Goodman.
• 13:20 – What drew him to Running Scared and Throw Momma From the Train?
• 15:50 – What was it like working with Rob Reiner and Nora Ephron before they started filming When Harry Met Sally? He also shares some great stories about the writing process and what it was like on set.
• 23:10 – Did they ever talk about a 3^rd sequel to Analyze This and Analyze That?
• 24:55 – Did they ever talk about doing another City Slickers sequel?
• 26:00 – What is Standing Up, Falling Down about?
• 29:00 – I read Josh Gad’s question.
• 30:50 – Prior to filming did he know what a Jägerbomb was? How he drank some before filming to see what it felt like.
• 32:20 – What was it like between takes with Ben Schwartz?
• 34:40 – How tough was it to get financing on Saturday Night which was his first time directing a feature film. Talks about how for 53 of the 72 day shoot he was in full makeup which meant working incredibly long hours.
• 38:30 – How Saturday Night was such an ambitious project for his first feature. Did he ever think he should have hired a director?
• 42:00 – He just directed Here Today with Tiffany Haddish. What is it about and when will people be able to see it?
• 45:30 – Shares a story about watching the first test screening of When Harry Met Sally with Rob Reiner.