Everyone either has or wants that cool uncle he/she gets to see at family functions every year. Luckily for those who fall into the latter category, Jack Splash and Bobby Caldwell took it upon themselves to fill that void with their beautifully smooth and funky music. You may be unfamiliar with Bobby’s name but you should be familiar with his music. His track “What You Won’t Do For Love” was sampled by J Dilla for Common’s “The Light,” and since then producers have been digging for early Bobby records any chance they get. Jack was one of those producers. But what brought them together instead of some other random producer and an underground legend? It helps that Jack has four Grammy’s under his belt and thorough experience leading a 15 piece band, Plantlife. He’s also been producing and writing for Cee-Lo Green, Alicia Keys, Kendrick Lamar, John Legend, and others. And the album that resulted from the two working together

This first offering from the newly christened project, Cool Uncle, is a mix of several genres that will undoubtedly have you grooving at work, on the train, or wherever you happened to be. Jack pushes the sonic boundaries of what you may have heard Bobby’s crooning over and it works as if the universe willed it. Take five or 50 from work today, stream some selections from the album below and read how the dream duo came to be and the process of creating the music.

Bobby, you used to do covers of Jimi Hendrix and Cream. How much did you enjoy those shows? Did doing those covers teach or help you with your career as you developed?

B: I was in bands since about age 14. I started off in my hometown, which was Miami. By 17 my band friends and I were in a van heading off to Los Angeles. We played the nightclub circuit. We covered everything from Hendrix to The Spinners. I played guitar, bass and did some vocals. There was a wealth of incredible artist to be influenced by and because I was like a sponge back then, soaking up everything I could learn. It became like a tapestry of everything I’ve retained.

You also portrayed Frank Sinatra in a musical. What was that experience like that for you, after working with other musicians who worked with Sinatra? Did that impact that way you saw Frank or in creating your own music?

B: At first it was a little eerie sharing the stage with people who had actually played for Frank, but in retrospect it was probably just me flipping on the mere notion of it. The impact that doing the “Rat Pack” had on me was profound as I gained a new prospective on him as an entertainer.

When was the first time you knew or heard “The Light” with Common and J Dilla? Were you pleased with the outcome?

B: I don’t recall when first I heard the song yet I remember being very excited about the track. My mother would have thought I should have been louder.

Jack, would you have done anything differently with the beat?

J: No way. Dilla is one of the few producers who usually did everything PERFECT. I wouldn’t touch a thing. Me trying to mess with that would be like trying to re-paint the Sistine Chapel. Bobby and I would rather work on NEW masterpieces and let the classics be the classics.

You stopped touring and then started writing and producing for other artists. Was there a particular reason for the change of pace?

J: Not so much a change of pace, because I always end up working around the clock whether I’m on tour (with my Funk band Plantlife) or in the studio. I can’t help it because I’m still in love with making music every day. The main difference though, is that when I’m producing other artists I get to push not just my own boundaries and limitations but the artists limitations as well. With an artist like Bobby Caldwell or Kendrick or Cee-Lo or Eric Biddines, their vocal range is so wide and their creativity is unlimited, so it’s really fun because each day in the studio is like a brand new experiment and you never know what you’re going to get. That’s the same thing with touring though…each new city brings different flavors and a different audience, so if you stay inspired on the stage you can have a REAL event and make something special happen each night.

Do you remember when and where you were the first time you heard Bobby Caldwell?

J: Yes, definitely. Well actually, I can’t really remember the first time I heard his MUSIC because “What You Won’t Do for Love” seems like it has ALWAYS been in my head and my heart, kind of like how certain Earth, Wind & Fire songs or Prince, Sly Stone or Marvin Gaye songs seem to always have been in my DNA. What I do remember though is that when one of my girlfriends broke up with me she immediately started dating this real slick dude who was going to take her to a Bobby Caldwell concert in Oakland (and that was only a few days after we broke up and it was one of their FIRST dates). My first question to her was, who the hell is Bobby Caldwell? Because at that time (like many other people of my generation), I only knew his music, but I didn’t know his name. She explained who Bobby Caldwell was to me, which only pissed me off even more because I LOVED his music but thought that the guy she was going to the concert with was a chump for doing something so romantic so early in their new relationship. Looking back now, I know I was wrong, but I’m glad I got my musical education, because after that I dug much deeper into Bobby’s catalog and found out that he was definitely one of my favorite artists of that era. So I guess I lost the girl… but I gained something more important.

Bobby, how aware are you that Hip-Hop is a big fan of yours, sampling your music for multiple songs? How do you feel about that?

B: I’m very aware, but more important than that, it’s really very flattering when an artist thinks enough of your work to sample it in the first place.

How did you guys come up with the name, Cool Uncle?

J: That’s easy. Because working with Bobby is like working with the coolest uncle on the planet. We had a lot of other VERY WEIRD names, but Cool Uncle just kind of stuck and made perfect sense.

How did you pick the guest features for the album? Bobby, how did you feel about them?

J: We both picked the people who we were friends with and who we truly thought would compliment the specific songs we put together. I know we BOTH instantly thought about Cee-Lo as soon as we finished our song “Mercy” because he just made SO much sense sonically & lyrically on that song. We also have a several more surprise guest artists who we plan on working with for the next album, but we want to keep that top secret for now.

B: As for me it’s interesting to note that the way this project turned and the great guest performances on it may well be what mandates the future of “Cool Uncle” as being a host, if you will, to future guest performances as Jack mentioned.

Bobby, how did you first find out that Jack was a big fan of yours? What made you decide to reach out and consider working with him?

B: It was an interview with Jack that came in on my wife’s Google Feed. He had mentioned me, as having been one of his influences, which was surprising given he’s about twenty years my junior. It was my wife who contacted Jack (believe it or not, through a Facebook page she set up for our bulldog), an impulse I thought at the time was a long shot, but Jack agreed to meet over dinner in Miami and we hit it off nicely.

Jack, what was the first thought you had when a dog’s Facebook account (AKA Bobby’s wife) messaged you?

J: It’s really weird because in regular social settings I’m very outgoing, but when it comes to music and dealing with artists that I REALLY look up to then I’m incredibly shy. I don’t know exactly where that comes from, but it is what it is. When Bobby’s wife Mary first reached out to me on Facebook, I think she did it from the account they had set up for their family dog!!! I honestly thought it was some weird practical joke from one of my nerdy music friends. Just in case it was real though, I had one of my assistant’s reach back out to get to the bottom of it. After a little communication, my assistant assured me that it really was Bobby & his wife and that they wanted to meet up with me. A few months later we had some drinks in Miami, chopped it up about our love for music and I guess the rest is Cool Uncle history.

What did you guys discuss the first time you met for drinks? How familiar were you, Bobby, with Jack’s work?

B: As I recall music seemed to be the main topic of conversation and then it rapidly progressed to drinking and laughter. I’d spent some time prior to our meeting familiarizing myself with what I didn’t know about Jack. We talked for hours and concluded at night’s end we were destined to work together.

What was the writing and creation of this project like? Were lyrics, melodies, and production created together or split 50/50? (I’m particularly interested in “My Beloved”)

J: For the most part we would just JAM. Just like I might do with any of my other friends who make music. It was really fun because I don’t think either one of us knew exactly what we were going to end up with. We’d sit down and really hammer out all of the lyrics and push each other to come with some really creative concepts. I almost ALWAYS defer to Bobby when it comes to vocal melody though because his instincts are so special and beautiful. I might catch something he was freestyling though and say “WAAAAAIT, we gotta lay that down.” Bobby does the same thing in reverse with me when it comes to the production. We get all of our ideas out and then he lets me go wild. On a song like “My Beloved” though, that’s actually the perfect example of us just having fun. We’re both Sci-Fi geeks and then I also think Bobby is a great example of someone who has drank from the “musical fountain of youth.” I mean his lyrical wit and his vocals are just as sharp as when he was in his 20s. It’s mind blowing to me. So in a roundabout way, I liked the metaphor of Bobby being this weird musical vampire who will stay ageless forever through his music. You throw in some alcohol and smoke and then “wallah” we have this really weird song that’s “kind-of” about vampires, “kind-of” about love and “kind-of” about staying young through music.

B: I think our exchange with one another is a perfect example of how great collaborations should work. When we embrace the other’s fortes you take away the boundaries, and that can have surprising results.

What are each of your favorite tracks on this album?

J: That’s a tough one because I like different songs for different reasons. There are so many different vibes on the album. Honestly, if I picked just one I would feel like I was being disrespectful to my other children/songs! What I will say though is that we TOOK OFF one of my favorite songs because I specifically thought that it was so weird and next level that it might piss off Bobby’s original fans. As a compromise, the album artwork for this first album is a subtle foreshadow of that song. We will definitely put that song out at some point (when I think people are ready for it).

B: I find something I like in all of the songs. When I wrote “What You Won’t Do for Love” so many years ago, I never thought it would be a hit. I leave it to the listeners to pick the favorites.

I get a feeling of combining so many artists (Chicago, Steely Dan, Dennis Edwards) but also putting a modern twist on them with little nuances like synths, bass, and sound effects that are commonly used in music today. Did you guys aim to educate the younger generation at all with this combination? Or you just wanted to make something that transcended time and genre?

B: I believe it transcended time and genre by default. It’s the sum total of our influences that makes “Cool Uncle” what it is. So you see it wasn’t by design, but by happenstance. At the end of the day that is what is so key to spontaneity.

J: That’s a REALLY great question and is actually spot on. I don’t think we specifically set out to educate the younger generation with mixing it up like that, but I guess in retrospect I hope it inspires them. So much music today sounds generic. Guys like Kendrick, J. Cole, Raury, Big K.R.I.T., Eric Biddines, etc. are pushing boundaries and I think that’s why people are responding to them. You can FEEL their spirit and their soul in the music. Really, the main thing that Bobby and I laid out for each other is that we wouldn’t have ANY restrictions whatsoever (musically, lyrically, etc.). None. Anything we felt like doing we just went for it. I mean in addition to all of the live instrumentation on the album, we used so many different types of synths and drum machines. We used everything from some of the OLDEST drum machines ever made (for their weird/unique tones) to the brand new ones. Just having fun and staying inspired. I didn’t realize it until afterwards, but that’s exactly how some of my favorite artists (like Sly Stone, Prince, Stevie Wonder, etc.) did it.

Projects like Cool Uncle give me hope that more and more artists will work with other artists outside of their genre and era. Why do you think it’s so uncommon? What needs to happen to facilitate that?

J: More dogs need to reach out to humans on Facebook. The world would be a better place.

B: I agree with you, Jack.

You can purchase the album on iTunes.

Bryan Hahn misses CD 101.9 FM now after listening to Cool Uncle. He’s on Twitter (@notupstate).