 Bob RossSelf (archive footage) | Self (archive footage) |
 Steve RossSelf - Bob's Son | Self - Bob's Son |
| VVicky RossSelf - Bob's First Wife | Self - Bob's First Wife |
| JJohn ThammSelf - Artist and Friend | Self - Artist and Friend |
| IIan BourlandSelf - Assistant Professor, Georgetown University | Self - Assistant Professor, Georgetown University |
| JJulia FriedmanSelf - Art Historian | Self - Art Historian |
| DDana JesterSelf - Bob's Friend | Self - Bob's Friend |
| DDoug BlandySelf - Author | Self - Author |
| SSally SchenckSelf - Director, The Joy of Painting | Self - Director, The Joy of Painting |
| GGary JenkinsSelf - Floral Painter | Self - Floral Painter |
| KKathwren JenkinsSelf - Floral Painter | Self - Floral Painter |
| AAndrea BaxterSelf - Crew Member, The Joy of Painting | Self - Crew Member, The Joy of Painting |
| BBert EffingSelf - Former Managing Director, Bob Ross Inc., Europe | Self - Former Managing Director, Bob Ross Inc., Europe |
| WWalt KowalskiSelf - Bob's Business Partner (archive footage) | Self - Bob's Business Partner (archive footage) |
| AAnnette KowalskiSelf - Bob's Business Partner (archive footage) | Self - Bob's Business Partner (archive footage) |
| LLawrence KappSelf - Former Employee, Martin F. Weber Company | Self - Former Employee, Martin F. Weber Company |
| WWilliam AlexanderSelf - Host, The Magic of Oil Painting III (archive footage) | Self - Host, The Magic of Oil Painting III (archive footage) |
