Since his career changing role 20 years ago in Clueless, Jeremy Sisto has worked steadily on film and in TV shows like Six Feet Under, Law & Order and Suburgatory. His latest project, which he also co-wrote and co-produced, is Break Point, a film about the tennis world.

In Break Point, Jimmy Price (Jeremy Sisto) is near the end of his career as a doubles tennis player. He decides to make one last ditch effort to revive his career and convinces his childhood partner – his estranged brother Darren (David Walton), now a world weary substitute teacher – to team up with him. The mismatched pair, with the help of 11-year-old named Barry (Joshua Rush), are forced to re-discover their game, both on the court and with each other. Break Point co-stars J.K Simmons, Amy Smart, Vincent Ventresca and Adam Devine.

Jeremy recently discussed everything from boob songs and homeless clowns and Clueless to his U.S. Open picks and, of course, Break Point.

You’ve been trying to get this made for a while. How did the project finally happen?

Break Point was something I was trying to make for many years. I was on a TV show all the time so I was trying to fit it into hiatuses. I was on network shows so I would only have three months [in between seasons]. There were three years when I thought the movie would be made and then there was a big letdown when it didn’t. When I finally had no other producer attached to try to get the money, I only had two months left before my hiatus, so it was going to be virtually impossible to make this thing happen. I figured this was my last chance or else the project was going to be dead after this hiatus for whatever reason.

I did what I vowed I’d never do again and that was to try to get money for a movie. I started talking to people and taking meetings. That’s not part of the process that I enjoy. I was very fortunate to meet Gabriel Hammond. He started Broad Green Entertainment. When I met him, he was just a guy seeing what the movie making this was. We partnered up on this and he was a great partner. To see now what he’s done with Broad Green is pretty exciting.

In the press notes, they mentioned that you would sing songs on the set. What songs did you sing?

I’m just always singing random songs. Half the time, it’s not a real song. I’d sing songs about boobs a lot – a lot of boob songs. Anyone who’s worked with me could probably recite one of my boob songs. I don’t mean to. It just comes out. It must be subconscious when I’m feeling at a loss for [singing] boobs!

Will you be dropping an album soon?

I did put out an album a few years ago from my alter ego, Escape Tailor.

Did you really?

Yeah. It’s like a homeless clown. You can check it out on YouTube. Enjoy.

How were you able to balance producing, writing and acting for the movie and what do you get from each?

As an actor, you feel like a tool, in a good way. You come to the game late and you leave early and you go to the Premiere and you take all the credit. It’s perfect. I love it [laughing]! I was craving to be involved in more aspects of the final product though. I enjoyed [producing] very much. There are certainly more areas at which I need to get better and areas that stressed me out more than they should have like trying to find the money, figuring out how to assemble a team. Then I had to figure out what to fight for when dealing with a budget and a schedule. You have to make some big decisions that as an actor, you don’t have to make. It was a great experience for sure.

The script came a long way in four or five years until we actually made the film. We wrote many drafts for different companies. It was fine because it was my first time. Inside, I probably didn’t feel like the project would actually come to fruition. To be here today [discussing the film] is a really big deal for me. It’s exciting to have some closure after so many years.

How did the script evolve over the years?

There was a darker back story between the brothers and their falling out that was filtered out in the development process. I think that speaks to the fact that we didn’t want to make the film overly dark and alienate [the audience]. We wanted to keep it grounded with real relationships and what families go through. Looking back, I think it was bold when we were hawking the script to not rely on something too broad.

Do you play tennis in real life?

I used to. I loved it before the movie [laughing]. I’ll get back to it eventually. David had been taking lessons since he was young. I didn’t play when I was young. In my twenties, every now and then I’d play, not very well. As the film became closer to actually being made, I took a lot of lessons. I mean a lot of lessons. I spent a lot of time on the court. I’d come out and David [Walton] would swiftly beat me. In tennis, like many sports, you have to start young to truly understand it. I’d have some moments where I’d be like, ‘I got it!’

I got pretty good at my peak, but there’d still be days where it was like, ‘how did I forget from yesterday how to do this?’ It really made me not like myself. I have to stay away from tennis for a while so I can like myself again.

Has your view of tennis changed after making the movie?

We watched a documentary called Journeyman I believe. It was about a guy very much like Jimmy. He never made too much money, but he was ranked and he would travel around the world on the tour and he’d get drunk and have a good time. He was basically [my character] Jimmy. It wasn’t a well made documentary. It was basically him with a hand held camera. That was the first time I realized what the life of a tennis player was about.

Through that and other conversations I’ve had, I learned that it’s a pretty lonely life, especially for a singles tennis player. That’s something you don’t really think about when you’re watching Wimbledon. You can see how lonely it is on the court when someone is fighting back after losing a set 2-6 or something. The doubles tennis world was something I wasn’t too familiar with. On TV, you just see a little clip about a doubles result or something. But doubles is a much more fun ride [on tour].

The Bryan Brothers will tell you that one of them was going to go off and play singles and the other was like, ‘maybe we should play doubles together.’ So the other had to decide to concentrate on doubles although the money isn’t quite as good. The life is just better.

How do you stay in shape?

I had to start lifting weight because of my role as a detective. I play a lot of basketball. That’s what I do. I had to go back to basketball [after the movie]. In tennis, if you’re having a bad day, it sucks for you and it sucks for the guy you’re playing because the points are short. In basketball, you can still get rebounds. You can still play good defense [if you’re having an off day]. I’ll be playing that until I twist my ankle again.

You’ve played many characters over the years, but as I’m sure you’re aware, it’s the 20th anniversary of Clueless. Did you have any idea that the movie would be so enduring and popular?

I did not. I’ve known for a long time now [laughs]. But no, when you make a movie, you never know. I remember having a conversation with Donald and Breckin saying, ‘well, some people might see it, but it’s not going to be huge.’ I haven’t actually watched the movie all the way through. Once my daughter is old enough to watch it, I might sit through it and appreciate it in a more significant way.

And you can embarrass your daughter with it too. That’s what you’re waiting for.

Exactly! I need as much of that as I can get for those teenage years.

Since this movie is being released during the U.S. Open, do you have any U.S. Open predictions?

Like I said, I’m taking a little break from tennis, but I like the older guys like [Roger] Federer. And [Rafael] Nadal. What’s going on with Nadal?

He’s having serving issues I think.

Yeah, I don’t know. The last time I was watching tennis which was a year and a half or two years ago, I was still into Nadal. It kind of saddens me. He could come back and have another moment. It’s important to have bad guys for me. Lebron James is a good bad guy in basketball. I feel like [Novak] Djokovic, I’m sure he’s a great guy, but Djokovic felt like a great bad guy.

Breaking up the Federer/Nadal stranglehold at the top?

Rivalries are always important in any sport, but especially in tennis. Personality is a big part of it. You get to watch someone maybe have a difficult time on the court – fighting for their lives it feels like. You see all the emotions going on in their heads. It’s a very interesting sport. I have so much respect for the game and the process of being a tennis player.

Break Point is now playing in select theaters and is available on Video on Demand.