Aired: 9/17/1999
Guest stars Spike Lee and D'Angelo
Aired: 9/24/1999
Guest stars Allen Iverson and Red Hot Chili Peppers
Aired: 10/1/1999
Guest stars Al Sharpton and Les Nubians
Aired: 10/8/1999
Guest stars Ilyana Vanzant and Mobb Deep
Aired: 10/22/1999
Guest stars Ken Hamblin and Me'shell Ndegeocello
Aired: 10/29/1999
Guest stars Colin Quinn and J.B. Smoove
Aired: 11/5/1999
Guest stars Don King, Dr. Dre and Snoop Dogg
Aired: 11/12/1999
Guest stars Taye Diggs and The Roots
Aired: 11/26/1999
Guest stars M.C. Hammer and Q-Tip
Aired: 12/3/1999
Guest stars Cedric the Entertainer and Nas
Aired: 12/10/1999
Guest stars Ananda Lewis and Kelis
Aired: 12/17/1999
Guest stars Marion Barry and Jay-Z