What is this film

[Brainworm]

During a discussion today I had a recollection of a comedy film (1990s I am guessing) where the main character was a risk averse actuary/insurance broker/ risk assessor.

The other main character was a wealthy guy who loved adventure and high adrenaline activities. Something happened that meant the insurance guy had to spend a couple of weeks (maybe a weekend) with the rich guy (to determine risk/ determine if they would insure him).

The wider story (inevitably) is that the uptight insurance guy learns to enjoy life more.

Does this ring any bells? My friends think I am probably remembering but from different films and thinking there was a single film. Google suggests they are right, but it's hard to believe it wasn't an actual film.

Any suggestions?

The Insurance Man?

https://www.imdb.com/title/tt11218768/#

Along came polly?

Sounds like Along Came Polly?

Or something from this list?

https://www.propertycasualty360.com/2015/11/04/25-of-the-best-insurance-movies/?slreturn=20240008154025

It sounds a bit like Along Came Polly...Ben Stiller being the uptight guy and I can't remember the name of the adventurer.

Along came polly?? He was a risk a assessor in it and someone who he assessed was rich and kept wanting to do daring stunts eg jump out of a plane.

I’m sure it’s Along Came Polly too.

Bryan brown was the actor who played the adventurer 😊

https://m.imdb.com/name/nm0000986/

Bryan Brown was in Along Came Polly.

Thanks All. It was Along Came Polly.

Weirdly, this came up when I Googled but I dismissed it because Jennifer Anniston didn't fit with my memory but I did recall Bryan Brown being in it. I guess I have blocked out the live interest aspect and recalled the other story line!

Thanks again, I can fall asleep tonight without it bugging me!