Deadbeat father. Quiz Kid Donnie Smith. 70's porn assistant director. Down-on-his luck car salesman who hires the wrong goons to kidnap his wife to collect some ransom money. These are some of the many prominent characters actor William H. Macy has played on screens big and little. Now he has something new to add to his prolific portfolio: filmmaker.

Last year, his directorial debut Rudderless had its world premiere at the renowned Sundance Film Festival. It had a small theatrical run and tomorrow it's available on DVD. I reviewed it while at Sundance and recommend adding this film to your collection.

Rudderless is a poignant and strangely inspiring movie about loss, pain, and bearing your heart to the world while coming apart at the seams. It stars Billy Crudup, Anton Yelchin, Felicity Huffman (Macy's beautiful and talented wife), Laurence Fishburne, Selena Gomez, and musician Ben Kweller.

Last week I spoke on the phone with Macy about his experience making Rudderless -- what worked and what he needed help on, and so forth.

Moreover, we talked about the MPAA, Shameless, and two films he co-starred in that had a huge impact in my life (as well as yours, I'm sure), Paul Thomas Anderson's Boogie Nights and Magnolia.

Chase Whale: Hey Bill, how's it going?

William H. Macy: Very well. Very well.

Excellent. Thanks for sending me a RUDDERLESS poster. Being quoted on it is very special to me.

Well then congratulations on your excellent taste. (laughs)

Congratulations on making an excellent movie! Let's go ahead and jump into this before time runs out. One major thing that makes the industry work is folks taking a chance or a leap of faith on others. As an actor you've done this with great success regarding acclaimed directors before they got all the acclaim most notably for a then unknown 20-something director with a little movie called BOOGIE NIGHTS. For your directorial debut, what about the RUDDERLESS screenplay made you want it to be your first leap of faith as a filmmaker?

The short answer is a lot of things fell together at the same time. It's my experience I read a lot of stuff that I think is worthy of being made that is difficult to get made. It's tough to get anything made but I read a lot of stuff. I loved the music. I loved that music was such a central part of it because music is a big thing to me. I loved the notion of dealing with violence. Talking about violence from a point of view that I don't believe has been covered in the past. I thought it was of a size that I could handle. I was a bit naïve on that part. It was a much bigger movie than I thought. I was talking to a friend about shooting on sailboats and he said, "Oh man it's a nightmare. Avoid it. Don't do it". Worse than that is music. But I thought it was a size that I could manage and then finally Keith Kjarval who produced it read the thing and he said "I can get this made" and he did.

Do you remember the moment when it hit you that you wanted to direct a movie?

It really wasn't a moment. I think I turned 50 or maybe when I turned 55 or something like that my wife said, "Well you're in your 3rd act what do you want to do with your career?". And with that (then?) my blood ran cold for a while. Third acts are so short. I think I've been coming at it slowly but surely. I love acting and I love the actors purview which is the minutia. You know we deal with really nanoseconds. Sometimes you'll do a scene where you really have one little moment and the whole scene is about 40 seconds long. I love that concentrating like that and I love having something difficult to do with 65 people watching you and as soon as you get it right they all get to go home. I love that pressure. Slowly but surely I wanted to be in charge of telling the entire story. I want to tell the whole joke. I want to set it up and throw the punchline myself. Other than thinking of minutes I thought, "Well I want to think about the whole world".

Now that you've made your first feature what have you learned as a filmmaker after filming wraps that you didn't know or really think about before shooting?

That's a great question. I learned a lot about. I had a great lesson about story structure and particularly set-up. I discovered that I thought the audience needed a lot more help getting into the story than they actually do. I shot a lot of stuff on set-up, on background that I ended up not using. I think I knew that somewhere in my DNA, but it was brought home. You know you want to get to the story as fast as you can [but you] really just need a couple of moments to give them their bearings and then you can go off to your story. In other words, you can say he's a successful business man. You don't need four scenes to prove it. Just say it.

That makes sense. Okay I want to talk a little bit about acting for a moment and then we'll go back to RUDDERLESS. These are throwback and it kind of goes into taking chances and this and that. Back to BOOGIE NIGHTS. It's such a filthy, but great story and a lot of amazing actors like yourself took a chance on it when Paul was super young and unknown. Do you remember what it was about the script that made you want to take a chance on starring in the film?

I was off working some place and I got this script and I read the thing and it was a lot more bold than the final product. I mean he had to tone it down a little bit. I called my agent and I said, "Am I being pranked? This is a porn film". There was just so much sex in it. He said, "No, no people really like this and you should see his first film which was called Hard Eight..."

Great movie.

I loved that it dealt with the porn industry. I feel like in this country we are so skittish about sex much to our detriment. I look at the MPAA board and the way they rate movies and I just feel like all of those people need therapy. They are allergic to sex which I find to be very good. Even the bad sex I've had is pretty good. And yet they are so permissive about violence, ugly pornographic violence. They think our 12 and 14 year olds can see that shit and I think they're sick. So Paul's film sort of was a half grapefruit in the face of our morals that way. It told a very interesting story with a good moral code at its core do you know what I mean? They're really good people.

Oh yeah absolutely. I really liked how they showed the madness and mayhem that goes behind-the-scenes of it and how it's not all glitz and glamour.

Man I saw Hard Eight and I walked out of the theater, it was a screening, and I said, "Dude if you want to direct the Yellow Pages count me in".

So going on another one of Paul's films you starred in one of the best films of the 20th century and the most important film in my life, MAGNOLIA. There's a rumor that Paul wrote most of the screenplay while at your cabin and I wanted to see if that's true.

I know he went up there to do one of his final drafts before going into production. There is usually a bit of a production draft that has to do with mechanics more than art. Yeah he went up to the cabin way out in the wild of Vermont and no one will bother you.

Regarding an important decoration of your character in MAGNOLIA, if you can remember, how many times did you have to listen to Gabriel's "Dreams" during shooting?

I guess I listened to it a lot, didn't I? Every driving scene, yeah... I thought you first meant that Aimee Mann song...

"Wise Up!"

I just loved that. And I loved his bit where everyone sang a little bit of it. I thought that was so novel.

Absolutely. "Wise Up" is an amazing song and that's one of the most fascinating scenes in film history. I could go on and on about that movie, but I know we're on limited time. So back to RUDDERLESS. You were talking about a little bit of the violence and everything. The film deals with a very sensitive subject, but handles it in a very professional and caring manner. How did you find the right balance with what happens in the beginning all the way with the rest of the story where everything eventually unfolds and plays out? You know some parts are funny. It's a really good balance of comedy, drama, and honesty.

WARNING: SPOILERS AHEAD.

Well I have a tendency to go for levity anyway it's just in my personality. I always look for the joke. I think it's a truism in this business if you really, really want to get people upset and emotional, get them laughing first. And the opposite is true also. If you want to really land a joke put it in the midst of a rather sad scene and then throw the joke. It sets us up. We knew, Casey, Jeff, and me, we knew that we were really playing with fire. One with subject matter. The big thing was are we trying to explain or excuse the kid and what happened? We went through great pains. There was a re-write late in the shooting where we had Laurence Fishburne say, "They were all somebody's kid and your boy killed 'em". We felt like it just needed to be said. It was just us bending over backwards to make sure we were telling the story we thought we were telling and that it couldn't be misinterpreted. The thing we were very aware of is that there is a great danger of being manipulative when you have a reveal like that and we moved it farther and farther into the body of the film before the reveal came. I felt compelled to make sure that I told the truth about everything you saw at the funeral and everything. I didn't want the audience to feel manipulated. As a matter of fact, I wanted them to look back and say, "Oh yeah it was all there. Nobody said it, but it was all there". I feel like we succeeded. I know I got raked over the coals by some press and I think they're wrong.

That's gonna happen. Like you said, they're wrong. I think you did a very...

You know everybody makes mistakes.

I think you did a very noble job with it. You were saying music is very important to you and music plays a very important part in the film. To me it became its own character. What was the process of building the (hit?) music that they play and most notably what made you want to bring on Ben Kweller? I'm a huge fan of his so it was a great delight, but why Ben?

Casey Twenter, one of the writers, said "you should see Ben". This was one of the first casting choices made. I think I saw him at the Wiltern and I heard him play and I said, "Ben I'm doing this movie would you read it?" and he said, "Yeah". I knew that the chances of me getting 4 accomplished musicians was thin, so Ben was my ringer. And in fact, he really helped the other guys Billy and Anton play but they are not professional musicians. He really helped us a whole lot. The process of finding the music. We hired a musical director named Liz Gallagher and she put the word out in the indie scene. You said it, the music is a character; the kid. So I put the word out that I wanted top songs. I wanted the audience to be able to hum the hook after just one hearing. I wanted them to be complicated. I wanted three parts: a chorus, verse, and a middle eighth as the Beatles called it. I wanted the lyrics to be funny and I wanted them to have irony and I did not want them to be about the movie. I said you can write about anything you want but not about the movie.

I actually know Casey and he told me to tell you hello because I told him that I was interviewing you today. Speaking of Gallagher because you mentioned the name Gallagher, I just wanted to say congrats on 6th season of SHAMELESS already being picked up. I think it's one of the greatest television families ever created. The first show where I love and give a damn about every character, congratulations on that. Congratulations on the film. Looking forward to everything you have coming up Bill. Great work.

It's a good season. Wait until you see it. Man, I finish big in this season too.

Awesome I can't wait. Well thanks a lot for your time and looking forward to everything in the future.

Thank you, Chase. Say hello to Casey for me if you see him before I do and thank you for your support man. Thank you for being there.

Absolutely. Thank you for making a great film.

I'm going to try to do another one.

Looking forward to it!

Rudderless is now available on DVD.

[Editor's Note: This interview was originally published on Twitch Film.]