Comedian Dane Cook’s half brother, Darryl McCauley, was sentenced to five to six years behind bars after he pleaded guilty to 27 counts of larceny, 3 counts of forgery, embezzlement and other charges on Wednesday (October 13).

The 45 year-old was Cook’s business manager for more than ten years (from the early 1990’s until December of 2008), when he began “transferring” millions of dollars from his brother’s funds into his personal accounts in 2004.

Darryl, who was a former corrections officer, must serve ten years of probation after he is released from jail and must pay restitution to his brother. Dane and Darryl are brothers from the same mother, Donna Cook, who sadly passed away in 2006.

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Aspiring singer Raquel Houghton has been reportedly dating comedian Dane Cook for a long time now. The couple first appeared together at the premiere of his movie costarring Jessica Simpson, “Employee Of The Month”, back in 2006 (photos below) but they have been keeping a low profile relationship ever since.

“We’ve been invited to other functions, but this is our first event of this caliber. This is my baby,” Dane Cook said of Raquel Houghton at the event who he described as “independent and funny — two things I like in a woman.”

Raquel is the lead singer of The Valli Girls and she was also an American Idol contestant last year (watch video below). There is no official information on the current status of Dane and Raquel’s relationship but we are assuming they are still together.

Raquel Houghton & Dane Cook Photos & Video Below go on reading »

Comedian Dane Cook took the stage at the 2009 Teen Choice Awards to present the Choice Hotties awards and made the mistake to poke fun of teen star Vanessa Hudgens and her involvement in a leaked nude photo scandal for the second time in two years.

Of all the bad cruel jokes that could have been made about a teen that is stupid enough to take nude photos of herself and send it to someone else, Dane was classy enough to just say, “Girl, you got to keep your clothes on! Phones are for phone calls, girl!”

I don’t see how that is offensive. It’s actually pretty good advice. Vanessa take notes. Dane was booed by the audience and later had to come out to defend his joke.

Dane Cook said:”I planned it about 20 minutes before I went out there because I like to be on the cusp of fear.

“My fans are very young as well, and everybody’s very opinionated. You gotta keep it classy… Mostly I just wanted it to be funny.

“That’s the best part about being a comic when you go, ‘Maybe I can say the thing that everybody is kind of feeling and nobody [is saying]‘. The elephant in the room moment. So, I’ll take it, I’ll take the hit. It’s okay.”

Was Dane Cook out of line? Why is everybody treating Vanessa like she is an innocent victim? Yes, what Vanessa did was stupid! And by the way, what the heck was Miley Cyrus thinking pole dancing like that at the TCA 2009??

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Dane Cook Vanessa Hudgens Joke Video

2009 Teen Choice Awards Winners & Photos At Gossip Teen>>

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Comedy Central aired comedian Dane Cook‘s new stand-up special, “ISolated INcident,” which will be released as an audio album Tuesday (May 19) and as a DVD later this year. Dane finally admits what America has been waiting to hear for years: “Can I just admit to you, you’re right,” the 37-year-old said, holding his palms up to the sky. “Look . . . I’m not funny. I’m OK with that. I’m cool with that.”

[video via ComedyCentral]

Dane Cook stopped by Yahoo!’s set yesterday to co-host their vlog (video blog), The 9 with host Maria Sansone.  Cook stars in the upcoming film, Employee of the Month with Jessica Simpson.

I dunno what Jessica Simpson was thinking with this black leather outfit. Perhaps it was an outfit for her sexcapades with Dane Cook.  It could also be her best Johnny Cash impersonation.  I just used Jessica Simpson and Johnny Cash in the same post. I feel I must go bathe now.

Did good girl-gone bad Jessica Simpson slip up and get pregnant? Well it appears she at least thought she did.

A panicked Jessica Simpson secretly took an at-home pregnancy test fearing she’d conceived a baby by new love Dane Cook, The ENQUIRER has learned.

“She definitely took an early pregnancy test and, knowing Jessica, she must have been freaking out,” a Hollywood insider revealed.

A surprise pregnancy by the single Simpson could have been the beginning of the end of her popularity. At least Britney waited to be married and we have seen Katie Holmes joy of being pregnant and having a child out of wedlock in Hollywood.

“Jessica is a good girl – and a surprise pregnancy isn’t something she could go to her agent or her parents about. And of course she no longer has Nick to confide in.”

Jessica’s rep denies it, but insiders say the pregnancy scare is the latest bump in Jess’ roller-coaster love life since she shed hubby Nick Lachey and launched a romance with Cook, star of the hit HBO comedy “Tourgasm.”

“Jessica was on the pill for years, but after she split with Nick and had no steady relationship, she went off it,” the insider confided.

After sticking the pregnancy test under her tongue, Simpson decided she was not pregnant.

Jessica Alba has signed on to star with comedian Dane Cook in Good Luck Chuck.  

Cook plays a serial dater who gets a reputation that any woman dating him will rebound into meeting her soulmate. When the man meets his true love, he must find a way to end the streak and keep her.

The film starts filming next month and will be directed by Mark Helfrich.