It's a rare occurance -- for a few reasons -- for Oprah Winfrey to host hip-hop stars as guests on her show, but yesterday (Sept. 24) she broke that streak.

She invited Jay-Z onto the program for a good, long segment on the rapper's career, as the two discussed their similar upbringings, the Chris Brown/Rihanna debacle, the "N" word, his father's abandonment and the Rocawear fashion line. He even tried to get the media mogul to rap, which was the second awkwardest moment on "The Oprah Winfrey Show" this week (behind only her interview with MacKenzie Phillips).

Oprah directly addressed the lack of hip-hop on her show by explaining her distaste for the use of "the 'N' word" in rappers' lyrics. Hov defended it, for his own lyrics, as a co-opting of a negative term for the positive, as a "term of endearment." Oprah added it up to a generational difference (she's 55, he's 39). The two shook hands, disagreeing. It was endearing.

Jay-Z also finally dished out what his advice was to his protege Rihanna, after her former boyfriend Chris Brown assaulter her in February. "She's young... it was either a situation where she can grow, and is a contention of young people that's going through the same sort of a situation and no-one is their voice. She can be their hero or she can choose not to grow from this. That's pretty much our conversation."

There was also the stroll through Mr. Carter's breeding grounds in Brooklyn's Marcy Projects and the two gabbing all the way up to his swank Rocawear offices.

And then Barbra Streisand sang. That was kinda weird.

Check out some clips below. The appearance will undoubtedly affect the sales of his new release "Blueprint 3" this coming week, after O exposed what this "hip-hop" music is all about to her rabid, loyal, middle-aged female base.