| Artist | Year at the Gathering |
| R.A. The Rugged Man | 2017, 2018, 2021, 2023 |
| R.B.S. | 2006 |
| R.I.A. (Real Industry Assassins) | 2007, 2008 |
| R.O.C. | 2016 |
| Raekwon | 2012 |
| Rahzel | 2012, 2013 |
| Rakim | 2024 |
| Ralphie May | 2012 |
| Randum | 2013 |
| Raven Black | 2021, 2023 |
| Razakel & Sicktanic | 2014 |
| Razorz Edge | 2013, 2014, 2018 |
| Really Bad People | 2022 |
Redefind |
2023 |
| Reflookoo Jambee Experience | 2007 |
| Rehab | 2006, 2010, 2012, 2013, 2019 |
| Reverend Fang Gory | 2007, 2008, 2009, 2010 |
| Rhythmic 3 | 2010 |
| Riddy K | 2019, 2022 |
Riff Raff |
2023 |
| Rittz | 2012, 2013, 2015, 2016, 2019, 2023 |
| Roach Joka | 2017 |
| Roadside Ghost | 2022 |
Rob Zilla |
2023 |
| Ron Jeremy | 2010 |
| Ronnie Blaze | 2017, 2018 |
Rook Mewsick |
2024 |
| Rouges Gallery | 2021 |
| Rowdy Roddy Piper | 2008, 2009 |
Rox-Tv Presents: Underground All-Stars |
2024 |
| Russett Burbank | 2008, 2010 |
| Rusty Nail | 2006 |
| Ruthless | 2006, 2007, 2008 |
Ruthless Rob |
2024 |
| Ruthless Underground | 2012 |
| Ryan Ho | 2012 |
Rysk |
2024 |
