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Jessica Simpson’s Ex Flame Dane Cook Congratulates Her On Engagement

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Dane Cook got more attention than he bargained for when he starred opposite Jessica Simpson in the 2006 flick Employee Of The Month. After being linked with the star, he had to work hard to adjust the focus back to his skyrocketing comedy career, which he was easily able to do by selling out arenas and seeing his sophomore release, Retaliation, debut at #4 on Billboard’s Top 200 albums chart, making him the highest-charting comedian in 27 years (last year’s Isolated Incident did the same, making him the only comic in history to achieve that feat). 

Cook, 28, just released a greatest hits set, I Did My Best — Greatest Hits, featuring his biggest guffaw-drawing bits and is on the road again with his Dane Cook Live! Tour.'s Charles Thorp spoke to him on my behalf to find out the methods to his madness and his thoughts on Simpson's recent engagement. What made this the right time to do a 'Greatest Hits?'

Dane Cook: I've had so many great new fans that just continue to email or approach me after shows, and ask what I would recommend they listen to. So I had the idea to put together something that's almost like a collection of highlight moments, which also says to fans that have been with me for maybe even upwards of twenty years, 'Thank you for all the support — here's a great gift for everybody.' I'm really, really proud of it; it's an incredible collection. 

Us: So it's like a love mixtape for your fans?

DC: It really is! That's the perfect explanation.

Us: How difficult was it to narrow it down? 

DC: I spent probably about a year listening. One of the weirdest parts was going back to a lot of the CDs of the demo stuff because I don't listen to a lot of my own material. Once I do a performance, I rarely go back and go over it. I think one of the most jarring aspects was my voice has changed quite a bit in the last ten years: it's gotten a lot deeper, and my Boston accent was much more apparent ten years ago. When you put everything kind of side-by-side, we've mixed tracks where it's like, okay, you can tell this one is a bit earlier because I'm ti-uhhed [breaks out Boston accent].

Us: Are there any comedians you look up to and respect, or try to emulate?

DC: There are so many guys that I admire, and I consider myself a student of the art of stand-up comedy. Growing up, we had old comedy albums in the house — we loved comedy in my household — so there was Cosby and Newhart and Carlin and I was watching shows like The Honeymooners and Jackie Gleason. All in the Family was my favorite show, and, I loved anything with funny people in and around it, I studied it, and I had an insatiable appetite for anything comedic. 

Us: Do you remember the first joke you ever wrote?

DC: Yeah! I have a lot of old notebooks and, that's kind of the next, mountain I want to climb. I'm actually putting a book together about my life in comedy, and what brought me to it, and some of both the highlights and some of the devastating, more traumatic things that have happened over the years that maybe people didn't even realize I was dealing with. It will show even more how important comedy was, and how much comedy gave me a life and saved my life in many ways. My 'thank you' list is long, and I'm incredibly appreciative of some of the people I've performed with and stood alongside. I've had some moments to sit and have moments with people I wanted to emulate, and some of my heroes that I've gotten to meet now, or dine with, and consider friends now. It's been a pretty incredible roller coaster ride!

Us: Any highlights you could share?

DC: I think one of the most exciting ones — and again, there's a bunch — but I will say that when I was at Letterman in mid-'98, it was my second time on the show, and Dave was out getting bypass surgery, which had happened kind of quickly. I was already booked, so I was still looking forward to the performance, even though I was upset and kind of worried about Dave. So when I got to the studio that day, I said, 'Oh, who's the guest host?' And they said, 'It's Bill Cosby.' And I was just over the moon. All of a sudden I get a knock on my dressing room door, and I hear [in Bill Cosby voice], 'MR DANE COOK IS IN THE BUILDING, LADIES AND GENTLEMEN. AND HE'S GONNA DO COMEDY ON THE SHOW WITH THE BILL COSBY.' And I turn around, I'm like, 'Oh my god.' He's standing three feet away from me. [Bill Cosby voice] 'Can I come in, Mr. Cook?' He was glowing with excitement, and he came into my dressing room. I remember everything about that meeting, but the two things that will forever be etched in my brain was, as he left the room, my dressing room, I said, 'Mr. Cosby, what's the key to success?' He turned around, didn't even miss a beat, and said, 'I don't know, I don't know the key to success, Mr. Dane Cook. But I know the key to failure, and that's trying to please everybody.' 

Us: I’d really like to hear one of your first jokes, maybe something that wasn't quite up to where you are now. 

DC: Hear it is, really simple. I was trying to be a joke writer, which has never been my forte — I've always been more of a storyteller with what I call 'JPMs,' or sometimes 'LPMs,' (laughs per minute or jokes per minute). I'm going to cringe as I say this, but I'll try to deliver it with as much gusto and aplomb as I can.'My uncle makes sculptures out of macaroni and cheese. It's a wonderful Kraft!' There are about fifty more exactly like that, which, I'm sure will also make me cringe.

Us: What's been your craziest tour experience so far, being on the road?

DC:  I will say, just standing in front of, on any given night, you know, ten, fifteen, sometimes twenty thousand people, it's just unbelievable. That energy stays with you, and as much as it's exhausting, it's kind of empowering and exciting and makes you want to get out there and do that night after night for that collection of people. My sister Kelly went to see a comedian I admire — Steve Martin — at Madison Square Garden. I was fifteen years old when she saw that show, and she came home that next day and was telling me about it. Right then and there I said, that's the kind of comedian I want to be. I told her that night, 'I'm going to play Madison Square Garden some day!' I wanted to be an event comedian, I've always wanted to entertain the world, These steps that I take are hopefully creating something that moves a mass of people. That's kind of always what I'm swinging for. 

Us: Well we'd like to ask you thoughts on a current subject. I'm sure you heard that Jessica Simpson is engaged, and you starred with her in Employee Of The Month. What's your reaction to that news?

DC: Well first of all, I did hear that, but I'm a massive proprietor of, you don't believe anything unless you hear it from the source. Jessica's a great friend of mine and I'm so happy for her! She's an incredible person and that's great, great news for her. I send out a big well wish to 'Special J' as we lovingly call her. 

By Ian Drew for To read more of Ian's blog, click here, and don't forget to follow him on Twitter.

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