Bill Simmons has never been shy to share his opinion on just about any topic, whether he’s an expert or not.

“It’s weird that San Francisco is so different now [compared with] where it was 25, 30 years ago,” Simmons said. “There’s a lot of reasons for that. I feel like Boston has improved in a lot of ways as a city. They’ve made it nicer, they added the Seaport, they had the Big Dig, it’s pretty clean.

“San Francisco feels like it’s in shambles compared to where it was 30 years ago.”

Simmons’ co-hosts on the episode, Sean Fennessey and Chris Ryan, immediately chided Simmons about this comment, with Fennessey replying, “You’ve been really involved in the legislative work there, the crime scene,” and Ryan adding, “Actively trying to get people recalled.”

But given a chance to back off after a cutting reference to Chesa Boudin’s recall, Simmons instead doubles down.

“The fact that the Nordstrom at the bottom of the hill, they shut it down, that’s like f—king amazing to me,” Simmons said. “That would be like if they shut down Faneuil Hall in Boston. Like, ‘Yeah, Faneuil Hall is gone.’ It made me nostalgic.”

The thing Simmons was most nostalgic for? The San Francisco of the era from “Axe Murderer,” the late ’80s and early ’90s.

“This was the best San Francisco time,” Simmons said, adding that he had friends who moved out there at the time. “… It was pre-Silicon Valley. There was still a coolness to it. A lot of young people were moving there or to Portland or places like that. You could still live there for cheap. You could get either a floor of a house or you could rent an apartment, but you could live three to four [people] to a place, and it was realistic.”

Simmons, a Boston native but a Los Angeles resident, seems to relate the city he yearns for through cinema, saying, “I think San Francisco is my favorite movie location place, and I say that as somebody who loves Boston.” 

“It’s such a cool city to shoot,” Simmons said. “You’ve got hills, you’ve got the water, you can see Alcatraz. It’s kind of creepy, but there’s also parts of San Francisco that look like you’re in Europe.”

Simmons also referred to SF as a “nooks and crannies” city, with neighborhoods that have a distinct feel. He even called Chinatown “amazing,” saying, “Chinatown in San Francisco is one of the best movie locations there is.”

“Axe Murderer” is more based out of North Beach than Chinatown, though they are right next to each other. The trio on the podcast clearly thinks highly of this movie, with Simmons calling the first 30 minutes “about as good as you’re going to do for a comedy.”

But in a way that is perhaps most fitting for Simmons, even that love for SF could only come with a call back to his personal home.

“This was a run of San Francisco movies, and it just seemed like the coolest place,” Simmons said. “I always felt like it was like Boston West.”