01. Spike Lee and D'Angelo
Guest stars Spike Lee and D'Angelo
30min
September 17, 1999
02. Allen Iverson and Red Hot Chili Peppers
Guest stars Allen Iverson and Red Hot Chili Peppers
30min
September 24, 1999
03. Al Sharpton and Les Nubians
Guest stars Al Sharpton and Les Nubians
30min
October 1, 1999
04. Ilyana Vanzant and Mobb Deep
Guest stars Ilyana Vanzant and Mobb Deep
30min
October 8, 1999
05. Ken Hamblin and Me'shell Ndegeocello
Guest stars Ken Hamblin and Me'shell Ndegeocello
30min
October 22, 1999
06. Colin Quinn and J.B. Smoove
Guest stars Colin Quinn and J.B. Smoove
30min
October 29, 1999
07. Don King, Dr. Dre, Snoop Dogg
Guest stars Don King, Dr. Dre and Snoop Dogg
30min
November 5, 1999
08. Taye Diggs and The Roots
Guest stars Taye Diggs and The Roots
30min
November 12, 1999
09. M.C. Hammer and Q-Tip
Guest stars M.C. Hammer and Q-Tip
30min
November 26, 1999
10. Cedric the Entertainer and Nas
Guest stars Cedric the Entertainer and Nas
30min
December 3, 1999
11. Ananda Lewis and Kelis
Guest stars Ananda Lewis and Kelis
30min
December 10, 1999
12. Marion Barry and Jay-Z
Guest stars Marion Barry and Jay-Z
30min
December 17, 1999