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We know everybody has an Aaliyah fantasy but this guy took his a lil too far. In a recent interview Hill Harper speaks candidly about being diagnosed with cancer, his latest book — on financial responsibility — and his multiple run ins with the late great Aaliyah Haughton — who he says had a thing for him. If that’s not enough bragging for you, he also claims he taught Obama how to dougie at his 50th birthday party.

After writing about youth and relationships, why did you target finance in your new book The Wealth Cure: Putting Money In Its Place?

Hill Harper: I was diagnosed with thyroid cancer. My father, grandfather and uncle all passed away from cancer. Money is meaningless without health. I realized that true wealth is a balance of physical wealth, emotional wealth, financial wealth and spiritual wealth. I was fortunate that it was detected early and last July my thyroid was successfully removed including three cancerous nodes.

What are the primary financial problems facing African-Americans?

Blacks have the least cross-generational wealth transfer. Each generation usually begins with little or no money. The best way to transfer wealth is life insurance. Take out a million dollar life insurance policy on your children so they can have that money. Another problem is credit card debt. If the credit card read “Slave” then people would throw it away. If you want Visa or MasterCard buy their stock.

You attended Harvard Law School with Barack Obama and remain good friends. Have you given him the book?

I planned to give it to him at his 50th birthday party, but decided it was not the appropriate time. It was a great party. We talked for a long time. I’ve attended several affairs at the White House that were very formal. This was casual. No cameras. We were just chillin’. I taught him how to do the “Dougie”, the old man version. [Laughs.]

Keep reading for Hill’s tall tale about Aaliyah and a tribute portrait by cartoonist Kevin Eason.

August 25th marks the tenth anniversary of Aaliyah’s death. “Try Again” is one of your favorites. Why is that song special?

She sang it for me! I met her at a party at Leonardo DiCaprio’s house. She was there with Kidada Jones, [daughter of Quincy Jones]. I was so nervous, my palms were moist. All I could do was say hello. I think she liked me but she was shy. The second time I saw her was at a Hollywood restaurant. My friend told her I had a crush on her. She told him she would come over to our table but when I looked up she was gone. Then I saw her a third time at a Baby Phat Fashion show in New York. I sat next to her in the front row. We talked and had a great time. So when she sang, “If at first you don’t succeed, dust yourself off and try again,” I did, and the third time was the charm!

Um, just what exactly is this guy trying to say? We’ve heard about him knocking down bad broads like Dollicia Bryan, but this one we’re not buying.

Good luck with the book though homie.

And while we’re on the subject of Aaliyah, artist Kevin Eason reached out to share this portrait he did of her:

Do you likey?

Kevin Eason is a freelance editorial cartoonist and illustrator from New Jersey. His brand of satire covers news events in politics, entertainment, sports and much more. Follow him on Facebook.

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