When I first interviewed Kenny Wayne Shepherd he was boy. He was part of the brat pack blues crowd that included Jonny Lang and Joe Bonamassa. Now, years later, I had the pleasure to chat with Kenny again. This time I spoke not to a kid guitar prodigy but rather to a young man of 33 who has his firm planting firmly on the ground and his guitar in his hands.

Shepherd has the soul of a bluesman and he has overcome obstacles that could have destroyed him including an ill-fated modern rock album flop and a bout with alcoholism. Instead of running away and hiding or pointing the finger at other people for his misfortunes, Shepherd bucked up and took responsibility for his own actions. He has now returned with a # 1 album on the blues charts titled Live in Chicago which was recorded on the heals of his award winning documentary 10 Days Out (Blues From the Back Roads).

By digging deeper into the blues and accepting that he was born to play this music, Shepherd has transformed himself from a hot shot, novelty guitar player into a virtuoso musician, willing to learn from his elders the true essence of the blues. I see only huge things ahead for the blond haired bluesman. Look for a new studio album in 2011 and check out the long awaited live album, Live in Chicago, to see what Kenny learned from his forays into the Southland.

Kenny Wayne: That was in New York City and I was on the Jimmy Fallon Show. Later that evening I also got to play it at the Beacon Theater in New York also. I was the first guy to play that guitar since Jimi Hendrix played it forty years ago. It was really every guitar player's dream.

Kenny Wayne: It really is any guitar player’s fantasy to be able to play that guitar. I was very honored and it really was a privilege to be able to get to do that.

Kenny Wayne: Trust me, after spending half the day with that guitar I could definitely get accustomed to hanging out with it. It really does belong in a museum. At the end of the day, it was not my guitar so I had to hand it back over.

Kenny Wayne: I have been playing Hendrix's music since I was a little kid. Jimi had a big influence on what I do. We have a great time doing that tour and that is why we have done all of these years in a row. Jimi is one of the best guitar players of all time and he has a huge catalog of hits you can choose from. We really do have a great time on that tour. There are no egos involved between all the bands and we really get to hang out a lot together. We get to hang out more than we would really get to on a regular tour. It is a pretty unique experience all the way around.

Kenny Wayne: It was something that we had talked about for a while. Originally we were just going to go down South and find some old school blues musicians and just kind of jam and tape them. I was even looking at it as a writing experiment to see if I could write with these guys. The idea just snowballed and we ended up going down there and making an album and a documentary film with these guys. It ended up being something that was bigger than anything I could have every imagined when we started. There are a lot of great people involved like BB King, Hubert Sumlin, Pinetop Perkins and all these other blues artists. I am really proud of it. I would have to say that it is really one of the biggest highlights of my career so far.

Kenny Wayne: I am a very big fan of the blues. Meeting, playing and hanging out with these people was a very humbling experience. It was very inspirational to me. These guys are my heroes and I was able to make an album and a film with them. I really think this will continue to inspire me for the rest of my life. I got to live out some of my childhood fantasies by playing with these guys and I am really proud of it.

Kenny Wayne: The fans have been really wanting a live album for many years. I think we gave them a very special album. It was recorded live at the House of Blues in Chicago and it was right on the heals of the Ten Days Out project. Some of the artists that were featured in that project are on the live album with us. The album is basically half live versions of the Kenny Wayne Shepherd Band and the other half is us jamming with these guys. We are playing songs that we had never recorded before. I think that is unique because most live albums are just songs you already know. Unless you were there that night then this offers the fans a new look at some songs they have not heard us do before.

Kenny Wayne: Exactly, man. I think the fans are digging it. Sonically, I think the album sounds great. The songs are good and the performances are really good. I think it stands up with any other live album out there. The fans have been wanting a live album for a long time and I think we have given them something that will really make them happy.

Kenny Wayne: I was sick. I had one of those 24-hour flu viruses that just about crippled me. I was curled up in a ball back in the dressing room. I had to cancel all of my meet and greets that evening. I really thought that for the first time in my life I was not going to be able to play; I thought I was going to have to cancel.

I got myself up off the couch and walked out onto the stage and the power of the crowd and the music was really strong. The adrenalin started going and I made it. I was really surprised when I listened back and discovered that my playing was really good that night. I really was pleased that I was able to play that well that night. I think it actually helped. I was so sick that I forgot that we were recording. It really ended up working to my advantage. When you know you are recording then you really can think about that too much.

Kenny Wayne: We are in the studio. We have been in and out of the studio about half the year between tour dates. We are hoping to have this out in early 2011. We are shooting for April. We are putting the finishing touches on it and we are just starting the mixing process. I'm am really pumped up about it. We had a great vibe and really hit a creative spurt. We have a lot of new material on it and a couple of cover songs that I think people will be interested to hear. It is really a solid record and it is really representative of where my band and I are at this time in our career.

Kenny Wayne: We have got Tommy Shannon and Chris Layton on it. It is really good. I am very excited about it. We put a lot of work into it and I know it will resonate with the fans.

Kenny Wayne: Everyone has ups and downs in their life. When you are met with challenges in your life it is all about how you meet those challenges that make you the kind of person that you are. I try to be the best that I can be. I feel a lot of responsibility has been given to me with my music. I have the opportunity to have a positive impact on people’s lives through my music. I try and stay as grounded as I possible can. I feel I am doing what I am here to do. I am very blessed because my fans are lifelong fans. As long as I am playing music and am true to myself and my fans then I feel I will be here. My career has been going strong since I was sixteen and I am now thirty-three years old, that in itself is quite an accomplishment in this business.

Kenny Wayne: I had a gig when I was about thirteen years old but I didn't have a band – I kind of did things backwards. My dad knew Buddy and I grew up listening to his music. My dad asked him and his band to back me up for my very first gig. I think he is an incredible guitar player and singer.

Kenny Wayne: Hubert is a legend. He is one of the most influential guitar players in the world. Eric Clapton, Jeff Beck, Jimi Hendrix, Stevie Ray Vaughan and others looked up to Hubert. They all copped his riffs, as did I. It was quite an experience to be able to play with him. The most valuable thing to me, however, is being able to call him a friend. We have a relationship and we talk to each other and we hang out a lot. Hubert is like a father to me. He is one of the sweetest people you can ever meet.