In "Finally a Lesson", Beast Boy mentioned that they were his "BFFs" and showed the other Titans a tattoo of their faces on his arm. He ditches the Titans to meet up with them and a little while later, he finds them doing graffiti on the city walls. They toss Beast Boy a can of spray paint and suggest for him to join in. Beast Boy refuses and tells them they would get in trouble for vandalizing city property. Then the Cool Rollerblading Dudes get angry at him and kicked him out of their group for not being "cool" enough and sprayed him with a can of spray paint and rolled away.
A few episodes later, they return in "Rad Dudes with Bad Tudes". While Robin was in awe of their awesomeness, Beast Boy who was displeased, and was the first one of the other Titans to refer to them as "grandpas". This could suggest Beast Boy remembers his short-lived friendship he had with them. Robin becomes saddened when he gets insulted by the Cool Rollerblading Dudes. Robin decides to become "rad" to impress them. He challenges the Cool Rollerblading Dudes to a race on the world's most dangerous rollerblading race, named "Demon's Tongue". The Cool Rollerblading Dudes accept his offer. Near the finish line, Cool Rollerblading Dude #1 (Chip) was having problems with the wheels on his roller blades. Robin offers to help him and lends him a hand. Just as Cool Rollerblading Dude #1 (Chip) was about to take his hand, Robin laughs and pulls his hand away causing the Cool Rollerblading Dude to lose total control and fall off Demon's Tongue Mountain. Later, before going to the hospital, Robin rubs his victory of winning the race in the Cool Rollerblading Dudes' faces while they visibly look unamused.
Cool Rollerblading Dude #1 (Chip) - He seems most likely the leader of the pack. He has brown hair and braces. He wears worn out white pants and a torn light turquoise jacket with a pink t-shirt underneath. He also wears a pair of shades with a pink frame. He wears light turquoise rollerblades with turquoise wheels that match his jacket. His clothing changed slightly in "Rad Dudes with Bad Tudes", as he wears a purple jacket with a light purple t-shirt instead of a light turquoise jacket and a pink t-shirt underneath. He also wears a pair of shades with a purple frame instead of shades with a pink frame. He also wears pink rollerblades with orange wheels this time instead of his light turquoise ones.
Cool Rollerblading Dude #2 (Randy) - He is the tallest. He has black hair. He wears blue shorts with dark blue leg warmers and wears a green tank top, and sports an orange and white sweatband. He also wears green rollerblades with orange and white accents and orange wheels. His appearance of his clothing changed slightly in "Rad Dudes with Bad Tudes", he wears a yellow tank top instead of a green one and wears orange shorts instead of blue ones. He also wears yellow rollerblades with white and orange accents with purple wheels.
Cool Rollerblading Dude #3 - He is the shortest. He has reddish brown hair underneath a brown hat. He wears a blue hoodie and tan pants, and a pair of shades with a blue frame. He also wears blue rollerblades with white accents and white wheels.
- Cool Rollerblading Dude #1 sounds very similar to Billy Numerous. The most likely reason is because they are both voiced by Scott Menville.
- Oddly though, there were a total of three Cool Rollerblading Dudes in "Finally a Lesson" but only two appeared in "Rad Dudes with Bad Tudes". However, Cool Rollerblading Dude #3 does make a cameo at the race at the end of that episode.
- It is revealed Cool Rollerblading Dude #1's name is Chip and Cool Rollerblading Dude #2's name is Randy.
- Chip has a similar hairstyle to Cody from the Total Drama Island franchise.