For the first time in their illustrious careers, Disney Music Group Chairman Bob Cavallo and his son, Warner Bros. Records topper Rob, have the same job. With the senior Cavallo set to retire from his post at the age of 72, his wife, and Rob’s mother, Judy, thought it was an opportune time for the two to sit down and go on the record.

Bob’s music business career stretches back to his years at Georgetown University, where he booked performers like Dave Brubeck and Dizzy Gillespie. He went on to run D.C.’s famed nightclub the Shadows (later the Cellar Door), before becoming a manager of bands like the Mugwumps (which featured future Mamas & Papas Cass Elliott and Denny Doherty, along with John Sebastian and Zal Yanovsky, whom he later managed as members of Lovin’ Spoonful). From there, his management clients included Earth, Wind & Fire, Weather Report, Little Feat and Prince (with Joe Ruffalo and eventually Steve Fargnoli), while founding the Third Rail management firm (employing Pat Magnarella), which boasted a roster that featured Alanis Morissette, Green Day, Seal, Weezer, Goo Goo Dolls and Savage Garden, earning more than 10 gold and platinum albums and numerous Grammys.

As a film producer, Bob was responsible for Prince’s Purple Rain and Under the Cherry Moon, then, and subsequently, with partner Charles Roven, such box offices successes as City of Angels, 12 Monkeys and Fallen. In 1998, Disney’s Michael Eisner and Joe Roth convinced him to take the helm of Chairman at Buena Vista Music Group, and he helped revitalize the company with hit acts like Hilary Duff, Miley Cyrus, the Jonas Brothers, Demi Lovato, Selena Gomez and Grace Potter & the Nocturnals.

Son Rob was born to the business, but didn’t follow in his father’s footsteps right away, choosing to major in English at USC, where he studied with novelist T.C.Boyle. As a kid, he learned how to play all the instruments on The Beatles’ albums, before remaking them in his home recording studio. A stint with George Massenburg at the Complex, the studio co-owned by his dad and partner Ruffalo, followed, before the young Cavallo joined the Warner Bros.’ A&R department, where he discovered and produced Green Day, tutored by the likes of Lenny Waronker, Ted Templeman, Tommy LiPuma, Russ Titelman and Richard Perry. He also produced hit songs like Morissette’s “Uninvited” and Goo Goo Dolls’ “Iris” for the soundtrack to his dad’s City of Angels, earning him a Producer of the Year Grammy in the process. His production credits include Fleetwood Mac, Green Day, Kid Rock, Jewel, My Chemical Romance, Eric Clapton, David Cook, Shinedown, Paramore, Lindsey Buckingham and the Dave Matthews Band. His work with Phil Collins on “You’ll Be in My Heart” for the Walt Disney feature animated movie Tarzan won him an Oscar, a Grammy and a Golden Globe for Best Original Song from a Motion Picture. He was named WMG Chief Creative Officer, before assuming the Chairman role for the Warner Bros. Records label in Sept. 2010.

A framed photo of father and son side by side on a beach, a mustachioed Bob and a young Rob, munching a Hostess cherry pie, intently watching a band named For Love or Money, adorns a desk in Cavallo senior’s spacious office on the Disney lot. “He turned to me and said, ‘Daddy, they’re not very good,’” remembers Bob. “He was already an A&R man back then.” As the conversation begins, we’re joined by his daughter (and Rob’s sister) Lisa, who does film and TV music licensing and marketing for the label, making it a true family affair.

Your wife Judy wanted to see this interview take place, while you were both chairmen of your respective companies.
Bob: It’s so unlike your mother. In my career, she’s never done this.
Rob: Well, this way she can control both of us at the same time.

You guys seem pretty competitive with one another.
Rob: I want a photo of us squaring off like this [puts up his dukes], with the boxing analogy… I’ve got the reach, but he has the quick hands. Way deep down inside, we want to kill each other.

Did you always know you wanted to be in the music business, Rob? Your father casts a long shadow.
Bob: He eclipsed that shadow a long time ago with the creative work he’s done. However, he’s still an irrational kid who needs his father’s guidance.
Rob: That’s why I’m going to hire him after he retires.
Bob: That would be worse than continuing to work. We are very competitive on the golf course.
Rob: We subtly like to know that we’re both killing it. We don’t really want to kill each other, but there’s a slight bit of...
Bob: It’s only natural. When Rob was 15 or 16, we had given him some equipment from the Complex, which Maurice White, Joe Ruffalo and I owned, and he started remaking the Beatles records, playing all four parts himself.
Rob: I did a punk-rock version of Prince’s “When U Were Mine,” when I was 16 and mixed it down to a cassette. The best-sounding stereo was in my dad’s car, this green Porsche 928. So I blasted it on his system, then left the cassette in the car. The next day, my dad goes to work, picks up Prince, who pushes in the cassette and on comes my punk-rock “When U Were Mine.” And my dad was like, “Oh, no” because Prince was looking pissed off. But he listened all the way through to the end, popped it out and demanded my dad tell him who did it. When he told him it was me, he said, “Why are you hiding him? I want him in Minneapolis.”
Bob: I didn’t want my kid doing that. Prince would’ve thought that school was unnecessary. He would’ve helped him as a musician, certainly, but then Rob would’ve been on the road, working, not sleeping and not educating himself so he could quote Wordsworth when discussing pop music in his interviews.

Rob, you majored in English at USC.
Rob: I was in my first band when I was 13, and we played all the clubs in Los Angeles. By the time I got to USC, I figured out I wasn’t cut out to be onstage, but I loved the music and the process. I ended up having a decently sophisticated studio in my dad’s house. Then I began to work at the Complex with George Massenburg in the early ’80s, where I first got the taste of the marriage between the technical and the musical. I very quickly began finding bands and producing them. My A&R ability got me a job at Warner Bros. Lenny [Waronker], Mo [Ostin] and Michael [Ostin] knew me through my dad. There was a band called Rhythm Corps from Detroit. The Warner A&R department was looking at them but weren’t sure they wanted to sign them. So I made a demo at the Complex for them and took it to Lenny and Michael. They told me I had made the band sound as good as they could, but it wasn’t quite good enough to sign. At that point, in 1987, they offered me a job in the A&R department for $500 a week. I found Green Day in late 1992, early ’93. For those six years, I got an incredible education. I feel I’m the last guy to come out of the Mo/Lenny A&R system. Ted Templeman always told me I was a producer, but I didn’t like the stuff they wanted me to work on. I learned the fundamentals from legends like Tommy LiPuma, Richard Perry, Russ Titelman—how to sign and drop bands, how to make a record. When I finally found my footing, I signed a band called The Muffs, made my first record and then Green Day found out about me, largely because of the fact I could play all those Beatles songs. We went in and made Dookie in 1994.

Bob, what did you see Rob doing as a career in the music business?
Bob: After I got him that first interview with Mo, it was all him. I was in awe of his talent. I couldn’t believe he could play all these instruments. He never took a lesson from anybody. He might have been shown a few chords by Lowell George and Zal. Rob studied creative writing at USC and wrote some good short stories. I remember him asking me, “Dad, what should I do when I graduate? Screenwriting or the music business?” And I said, “I think what you do in music is more remarkable than what you do as a writer.”
Rob: I was a double major in guitar and engineering at the Grove School of Music. The advanced theory came easy to me.
Bob: I obviously steered him right. What I loved about Rob was, he went and figured out what was happening electronically and internally in a piece of music, from a theoretical point of view. He even studied the physics of sound, which prepared him for his career. When Green Day fired their management, he suggested they go to his dad’s company, Third Rail. So I was basically handed an arena band. It was the only artist I ever had served up to me like that. I also produced a movie, City of Angels, with my partner Chuck Roven. Danny Bramson kept trying to get me to put music in it, but I thought it wasn’t cool enough. Rob goes in, sees the film, and brings in Alanis Morissette and the Goo Goo Dolls’ Johnny Rzeznik. By the following Monday, he had hit songs with both of them.
Rob: It was a fun thing because I knew Johnny’s song [“Iris”] totally embodied the Nicolas Cage character, while the Alanis song [“Uninvited”] captured the Meg Ryan role. I remember certain powerful people were all freaking out, telling me I was ruining Alanis’ career. Those two songs fought each other for #1 on multiple radio formats for six weeks. City of Angels is the second-biggest soundtrack on Warner Bros. of all time, right after Purple Rain, so the Cavallos hold the top two.
Bob: I still get a royalty from the City of Angels soundtrack.
Rob: The domestic gross on the film was $80 million, while the soundtrack earned $140 million. I ran into Nic Cage in a bar once and joked with him about that.

What one thing do you take from your father’s career that helped you along the way, Rob?
Rob: It’s pretty simple. He told me it’s always about the quality of the music.
Bob: It’s all about honesty. You have to be honest with the artist and the music, which has to tell some kind of truth. All those things weren’t necessarily stated, but they were available to him.
Rob: I have so many amazing stories. I remember, when I was six, driving with him to Philadelphia to see a band when we still lived in New York. We listened to the radio all the way, and he asked my opinion on each song, discussing which ones were great and why. He took me on tour when I was 11 to see Earth, Wind & Fire, the greatest stage show I think I’ve ever seen, just phenomenal musicians. I was exposed to amazingly good taste at an early age.

Do those same truths apply as the music business enters a tentative future?
Bob: I’m the last guy in the world to ask about this. I’ve lost a little bit of faith in the quality of the art. There aren’t too many records that completely blow my mind anymore. Of course, we can blame it on the fact I’m an old fart, but I don’t think it’s as great as it was back then.
Rob: I feel slightly different. It seems the really, really great stuff isn’t occupying the country’s attention or the social media attention, Adele being the exception.
Bob: There are a few I do respect, like Lady Gaga, who is the real deal.

For two guys who cut their teeth on classic rock & roll, it must be depressing to see the genre wane as a commercial force.
Rob: I actually think rock & roll is always primed for a great record to be made, and I try to make them. I encourage the bands I work with to think big, to think they could do something artistically credible that both satisfies them and can sell records. More artists should think like that. In some ways, the connection to real musicianship—and not just relying on the computer—is coming back. Over the last three or four years, the rock world has gotten hurt by making records that sound very much the same, and only shooting for a small audience. Pop music is always evolving and doing its thing. There are a great many bands who’ve come to our attention at Warner Bros, who are in their mid-teens, playing rock on their instruments and doing it brilliantly. It’s a reaction to all these straight-ahead, down-the-middle pop things.
Bob: I’m a big believer in Grace Potter, who is great. I also have a young girl rock band, Cherri Bomb, who are remarkable, about to put out their first album. Nathan Pacheco is another promising artist in the mold of Josh Groban and Andrea Bocelli.
Rob: Here come the plugs.
Bob: I haven’t gotten a word in for the last 10 minutes.
Rob: We have a female singer-songwriter, Neon Hitch, who is absolutely fantastic, a true star. And we have a rock band called The Indecent from New York whose average age is 16. I played it for Bob during my first month at Warner Bros., and he told me I have to sign them.

Do you still produce records, Rob?
Rob: I’m basically wearing three hats, as Chairman, A&R and producer. People think I’m crazy, but I love it. I’m actually more in touch with all aspects of the business. You actually become aware of so many things, that one hand helps out the other. As a Chairman, I get to judge the overall marketing and sales for a project, which I can put into A&R, then educate the artist as to what they’re up against.

Bob, the 13 years that you’ve been Chairman of the Disney Music Group have made a nice third act to your career.

Bob: That’s exactly what Michael Eisner said it would be when he was trying to convince me to come here. I’ve never had a real job working for somebody else. I’ve always had my own company. I was kinda part of the ’60s counterculture in that way. I didn’t think I’d ever work for a large corporation. Secretly, I was fairly conservative. I was soured on the movie business. I had a period of ennui, and when I was approached by Disney to take over Hollywood Records, I took the challenge. I was afraid, but I had nothing to lose. I was starting at the bottom. It was a rugged first four years. They came close to shutting us down. Bob Iger saved us, we made money the next year and then a lot of money over the following 10 years.

How do you see the future of the major label system?

Rob: It isn’t what it was 10 years ago, but we’re doing fine. There has been erosion in terms of sales, but at the same time, the last two years have been pretty good. I believe in the 360 model. I’ve seen it work. We will make twice the money with Paramore’s third album than the second, even though it didn’t sell nearly as much. In any other business in the world, if you’re putting 100% of the money in, you should enjoy some taste of the multiple income streams.

Bob: I can’t believe you’re having this conversation with him while I’m sitting here.

Rob: He’s the king of it. He started it.

Bob: We’re probably the first company of any stature to do 360 deals with acts like Miley Cyrus and the Jonas Brothers, who were selling out tours which we had a piece of. My argument is, if we’re helping you build a brand, we want to be your partners. I had to do whatever it takes. And I wanted young artists to see this as a good place to be.

How proud are you of Rob’s success?

Bob: Stupid proud. He plays me some great music he’s worked on, and tells me what he’s contributed, I’m just amazed and humbled by his talent.

Rob: He tells other people, but not me. But I’m amazed at his. This guy has picked every hit record at Disney for the last 14 years. Think about that. He has perfect pop taste, which is unbelievable. He signed Earth, Wind & Fire from the very beginning, when Maurice White was just a drummer who wanted to start a band. He managed Weather Report. He recognized how great the Lovin’ Spoonful was.

Rob: He was the one that picked “Time of Your Life” as the second single from Green Day’s Nimrod. Everyone at Warner Bros. was afraid of putting that out, thinking that it would alienate the band’s core. Bob convinced them it was the right song to release.

Bob: Hey, I used to sell Catholic magazines door to door. If you could do that, you can do anything.

Rob: In my opinion, that made American Idiot possible, and allowed Green Day to be thought of as a larger band. It took awhile to consolidate those two audiences. There were definitely people who bought that record expecting 10 “Time of Your Lifes,” and found just the one.

Bob: We also convinced Warner Bros. to release “When Doves Cry” as the first single from Purple Rain. There was this big scary Urban promotion dude at Warner who wanted to go with “Let’s Go Crazy.” But we thought “When Doves Cry” was a work of genius. So we started arguing, and we eventually won, because Prince was on my side. Prince loved me because, if there was a lyric in one of his songs I thought was cool, it was usually the same line he was proud of. We also told him he needed a single for the album that would be 1999. After calling me the “White Rabbit,” which was pretty insulting, he went away and came back with “1999.”

So January 31 is your last day at Disney Music Group.

Bob: I’ve been working for 60 years, since I was 12, when I used to go to the bakery in Yonkers at four in the morning on weekends, and scrape the pans after they cooked the first batch of pastries. Then I went to the newspaper and collated all the individual sections for delivery. Everyone is so worried about what I’m going to do. The only thing I’m worried about is how I’m going to run my life without a fulltime assistant.

You’ll play more golf, then?

Bob: My handicap was in the single digits for 25 years. When I came to Disney, I quickly went from 8 or 9 to 13, 15 and 17. I have to go back to playing golf three or four times a week, like when I had my own company.

Who usually wins between the two?

Bob: We haven’t had a blood match in quite a while, but we have a game every Saturday at El Caballero in Tarzana.. He has more talent than me, but he can’t beat me yet if we’re playing seriously. His swing is so gigantic, he’s about 100 yards ahead of me on every hole.

Rob: I hit the ball too far, and I can’t control it. It goes way far left or right. And then I’m in trouble.

Bob: I won’t ride with him, because his cart goes where no man has gone before. He’s never in the fairway.

Rob: My favorite thing is meeting Dennis Lavinthal at the first tee on Lake Arrowhead Country Club and rubbing his belly for luck.

How do you feel about seeing your father step down?

Rob: I think he’s worked so long and so hard. It’s time for him to enjoy, not have any stress and take care of his health.

Bob: I want to go to Hawaii and not know when I’m coming back. I want to enjoy my three grandchildren. Judy and I haven’t done any traveling that hasn’t been on a schedule. Let’s say, six months from now, I’m bored. What if I bought a business? It’s hard to earn money on your money these days.

How about acquiring HITS magazine?

Bob: No, I want to make money. I haven’t had time to think about the economy if a Republican gets to be President. That could be a bonanza financially.

You’re rich enough to be a Republican, Bob.

Bob: Quietly, while I sat at the Kettle of Fish arguing with Phil Ochs, I was really a closet capitalist. I voted for John Kennedy in 1960 when I was 21 years old. But I voted for a Bush, also. I believe in the Constitution. I don’t give a shit about stuff like gay marriage. On social issues, I’m 100% liberal. If we have to put some money aside for people who are less fortunate, that’s fine. But when they say it’s unfair for people to make a lot of money, I go, “Wait a second.” When did the government get the power to decide what people should own or not? I’ve never said this at Disney because everyone’s liberal here.

Rob: I’m a centrist with a slight right lean because of him. Mostly just on economics.