| Name | First Aired | Runtime | Image | |
|---|---|---|---|---|
| S04E01 | Spike Lee and D'Angelo |
September 17, 1999
|
30 | |
| S04E02 | Allen Iverson and Red Hot Chili Peppers |
September 24, 1999
|
30 | |
| S04E03 | Al Sharpton and Les Nubians |
October 1, 1999
|
30 | |
| S04E04 | Ilyana Vanzant and Mobb Deep |
October 8, 1999
|
30 | |
| S04E05 | Ken Hamblin and Me'shell Ndegeocello |
October 22, 1999
|
30 | |
| S04E06 | Colin Quinn and J.B. Smoove |
October 29, 1999
|
30 | |
| S04E07 | Don King, Dr. Dre, Snoop Dogg |
November 5, 1999
|
30 | |
| S04E08 | Taye Diggs and The Roots |
November 12, 1999
|
30 | |
| S04E09 | M.C. Hammer and Q-Tip |
November 26, 1999
|
30 | |
| S04E10 | Cedric the Entertainer and Nas |
December 3, 1999
|
30 | |
| S04E11 | Ananda Lewis and Kelis |
December 10, 1999
|
30 | |
| S04E12 |
Marion Barry and Jay-Z
season finale
|
December 17, 1999
|
30 |
No artwork of this type.
No artwork of this type.