| Artist | Year at the Gathering |
| Waka Flocka Flame | 2015, 2017 |
| Warren G | 2010, 2012, 2016 |
| Wayne Static | 2014 |
| Wazteland Warriorz | 2013 |
| Whiskey N Water | 2021 |
| Whitney Peyton | 2010, 2013, 2014, 2016, 2019, 2021 |
| Who's Bad | 2012 |
| Wicked Wayz | 2011, 2012, 2022 |
| Wiked Wood | 2017, 2021, 2022 |
| Wil & Rabbid | 2015 |
| Wil E. Haze | 2017 |
| Wild Bill | 2022 |
| Wild Onez | 2012 |
| Wildcard | 2013, 2014 |
| Will D.O.E. | 2013 |
| Windy City | 2015 |
| Wizard Of The Hood | 2016 |
| Wolfpac | 2004, 2006, 2007, 2008, 2009, 2010, 2011, 2012, 2013, 2014, 2015, 2016, 2017, 2018 |
| Wreckless | 2007 |
