A week from now, Wednesday March 18, 2009, XXLMag.com is set to premiere its directorial debut for "Loser," a cut off Charles Hamilton's recently released The Pink Lavalamp.

Documenting rougher times in Charles' life, the 15-song disc was recorded at Frederick Douglas Academy- one of the key locations featured in the clip. The video was also shot at Angels and Kings, Pete Wentz's (of Fall Out Boy) famed night club, among several other locations throughout New York City. Here, we chop it up with Charles, his manager le'Roy Benros, Harris Publications executive publisher Jonathan Rheingold and XXL executive editor Vanessa Satten to break down how the two parties joined forces to produce the video.

XXL: So how did the video come about?

Jonathan Rheingold: The video came about in a conversation I had with Theo Sedlmayr who's Charles’ attorney. Theo gave me history that Charles, prior to his deal with Interscope, had this recording [The Pink Lavalamp] he did when he was really into doldrums basically utilized his school facility and did the entire recording at the school, in his public school in the basement and he said he was releasing it as somewhat as a prequel to his life so people, so the fans now would be able to dive deeper in his past. As a matter of fact, it’s kind of like the Star Wars story where they’re telling you the origin first before the main record comes out because Pink Lavalamp is out now and his record with Interscope is yet to be released. We felt like we needed to do something that was really unique. It’s really just to do something unique for the site, help foster Charles’ career.

le'Roy Benros: Well we definitely wanted to do something unique to present this video. The song "Loser" has special meaning to Charles so we don’t wanna just do a video and release it, we wanna put a story and no one’s better than XXL to partner with to write about the story and do a visual at the same time. So we approached XXL about doing the video and they liked the idea and we made it happen.

XXL: What was your reaction when you first heard that XXL wanted to do your video?

Charles Hamilton: I was very happy about it, you know. And the people on my team can tell you that I’m not a big fan of shooting videos and having to pose and change clothes but the song “Loser” the visual that I had for it, that I had for years, ironically the director [Travis Satten], he had the same vision. So it was like "oh wow," obviously there’s only one way to look at this song. And the fact of the matter is they liked that song so much that they wanted to shoot the video. They were able to shoot me in my natural element and we had fun doing it so it was like "wow." Everything was just coming together so naturally, nothing was forced. Everything was all smiles at the shoot. It was crazy.

XXL: Some people will probably see a conflict with XXL doing Charles' video, but times have changed. Why do you think it works now?

JR: I think it’s a really good precedent in terms of a magazine taking a new type of role in promoting an artist because while our magazine, our website always will operate through brand XXL is always about journalistic integrity. In the case of Charles where we feel he’s a true talent, why not be a part of fostering his career and being part of that discovery. You know a magazine that endorses an artist, I think there is somewhat of a line in the sand. We’re able to cross that line and produce the video because you know we have a website, times have changed and we wanted to create our own content beyond the magazine and that seemed to translate into video.

Vanessa Satten: I mean it’s surprising to me. I never looked at it as a conflict of interest. We need to step outside of our box like a lot of different websites and magazines are. So we just had to find a new way to present something and see if it works. Instead of us sitting down and giving you a Q&A or something like that , which you can get anywhere, it’s letting us provide something, or sitting down and listening to a banger, it’s letting us provide that stuff in a new way. The song tells the story of Charles, the song "Loser," his lyrics tell that he once was a loser, he still is a loser but people like him now. The video is trying to tell that story just like the magazine tries to tell someone’s story. So our goal was to take a story and put it into video form.

le'Roy: It really has to do with the magazine's support of the artist, they believe in the message the artist is trying to bring. We weren’t gonna do the video if the outcome result wasn’t to show Charles in the light we want him to be seen in. We went along and we were on the same vision and we made it happen and it came out really well and I think it really shows Charles in the light we want him in from the stages he came from, to where he’s at now. I just think that as long as the partners involved see the same vision then we can make it happen.

XXL: So what was it about the song “loser” that you wanted to do the visual for that one? I know you said you’ve had it in mind for years, why’d you pick that one specifically?

CH: I mean, right now, this is the position I’m in. I’m 21, I’m known as the pink-wearing, Sonic the Hedgehog obsessed guy and I’m supposedly not going to make it past March in hip-hop. At the same time I was just on the cover of XXL magazine, Fader magazine and I was just on Carson Daly. So I’m somewhere in between loser and the next big thing. I’m really just your average Joe. At the same time, for that song, it’s like, ‘oh by the way, I knew ya’ll niggas was gonna call me a loser for this shit.’ I made the song like 2006, 2007. So back then I knew like I was gonna get in the game and from the status quo, anti-young people backpackers to the not so status quo, what the hell is a backpacker, ignorant kid in hip-hop. They all kinda have to look at me and say, "this dude is a loser, but I fuck with him."

XXL: I know you had Fredrick Douglas Academy in the video. Why was it important to you to have that backdrop in this video particularly?

CH: Because that’s where I recorded the song “Loser.” That’s where I recorded most of the songs before the record deal, I recorded in FDA. So that was like let me take ya'll home right quick, like literally take ya'll home. I used to live in Fredrick Douglas Academy so let me introduce ya'll to my house and my living arrangement before I got the deal. I mean, just to show ya'll how real it is…I can almost tell you there was no treatment, like we literally went to three set locations that I really wanted, the video was like real TV, dead ass. Like, the video is really spots and locations where I was in my life. So as much as it’s a video, it's like a documentary for me. And the funny thing is, in the video, the two homeless dudes, like I knew them. We know each other from back when. Those is my dudes right there. So this wasn’t an on set, "yo, we need two homeless guys," like, they said we’re shooting a video for this guy named Charles Hamilton. "Charles Hamilton?" Hey, why does that name sound so familiar? Charles Hamilton, hey let me see that boy." So I come walking over to them, and they’re looking at me with the same look I’m looking at them. Like, "get the fuck outta here. No way are these guys still here." And they’re looking at me like, "no way is this guy shooting a video." And I think we have the conversation on video still. We were there kicking it like it's old times. So it's crazy watching that video. And like, I love the song even more now. It’s hard for me to like “Loser” more than I do but like all the things that I’ve seen as far as listening to that song now, the visual has come to fruition. So it’s just another confirmation that dreams come true. Which is why I just cover my ears and ignore all the hate.-XXL Staff

Make sure to come back tomorrow for more on the making of Charles Hamilton's "Loser" video. The clip premieres Wednesday March 18, 2009 at 10 a.m. EST.