1. Spike Lee and D'Angelo

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. 17 September 1999. 30 min

Guest stars Spike Lee and D'Angelo

2. Allen Iverson and Red Hot Chili Peppers

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. 24 September 1999. 30 min

Guest stars Allen Iverson and Red Hot Chili Peppers

3. Al Sharpton and Les Nubians

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. 1 October 1999. 30 min

Guest stars Al Sharpton and Les Nubians

4. Ilyana Vanzant and Mobb Deep

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. 8 October 1999. 30 min

Guest stars Ilyana Vanzant and Mobb Deep

5. Ken Hamblin and Me'shell Ndegeocello

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. 22 October 1999. 30 min

Guest stars Ken Hamblin and Me'shell Ndegeocello

6. Colin Quinn and J.B. Smoove

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. 29 October 1999. 30 min

Guest stars Colin Quinn and J.B. Smoove

7. Don King, Dr. Dre, Snoop Dogg

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. 5 November 1999. 30 min

Guest stars Don King, Dr. Dre and Snoop Dogg

8. Taye Diggs and The Roots

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. 12 November 1999. 30 min

Guest stars Taye Diggs and The Roots

9. M.C. Hammer and Q-Tip

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. 26 November 1999. 30 min

Guest stars M.C. Hammer and Q-Tip

10. Cedric the Entertainer and Nas

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. 3 December 1999. 30 min

Guest stars Cedric the Entertainer and Nas

11. Ananda Lewis and Kelis

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. 10 December 1999. 30 min

Guest stars Ananda Lewis and Kelis

12. Marion Barry and Jay-Z

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. 17 December 1999. 30 min

Guest stars Marion Barry and Jay-Z