There's an outsized mention of "generations" in rollerblading lately; particularly on the Fungus Knifing Talkshow, but none have thus far attempted to loosely or discretely define said generations. Based on my limited knowledge, gut instinct, and personal biases, I'll give delineation a try so that we can 1)anecdotally bucket-label eachother and 2)make fewer unwarranted experiential assumptions of our near-peers' assumptions.
GENERATION O - THE LAND BEFORE TIME : 198X+
Rollerblade... the ride continues
Arrived with the first wave of Rollerblade® product and took more cues from rollerskating than skateboarding or BMX. These guys (and a shockingly high percentage of gals- relative to the twenty plus years o' participation between then and now) were freestyling ahead when grinding on blades was just a sleazy dance a la 1987.
Team Rollerblade's Doug Boyce, AJ Jackson, Pat Parnell, Alan and Donna Vano, Chris Mitchell, -insertdozensofsemilegendarynameshere- wowed the crowds with synchronized footwork and novel vert ramp under-over passes. I'll make up some statistics here which indicate no more than fifty of these folks are still inline rollerskating with regularity today, worldwide! Those that do have long since dissociated from "aggressive" if ever they did.
The opportunity cost for this bunch was incredibly low (since there weren't many participants, let alone competition) and those capitalizing early probably made some real money for a couple years before the cutthroat frontflip kids dropped in and rad fly away-ed with the tradeshow checks. Gen Zero demo squads might have earned as many inflation-adjusted United States Dollars from a week of dance performances as Nitro Circus today pays Euros in half a year.
GENERATION I - JURASSIC PARK : 1987+
Prototypical petri aggressive inline skaters. Some overlap with Gen 0, but defined by angsty punk recalcitrance. Attempted X-crossovers from Gen Zero probably looked as silly to the core of this bunch as Mo did in this K2 ad:
Gen One put down the rollerboards to pile the spandex into a flaming neon heap and forged in it grind plates from skate wrenches. Many would later go on to become the reluctant immortal superstars of rollerblading. Latecomers in this group called it quits after only a few years to participate in the next decadent 90s trend of which there were many.
GEN II - LADYE BEARD : 1992+
Performed a sidewalk on a 5-stair handrail wearing 34" ankle opening JNCOs sporting a lampshade hat ordered from Team Paradise, but not before perfecting the heavily padded Chris Edwards look lounging in a tumble-dried pair of Crashpads while watching Hoax II on repeat for a month straight. 18 Days Schrijn kinker soul to switch soul has meaning.
Unrelenting, brutally effective mass media megacorp consumer marketing convinced this group that soul grinding was spiritual. Present-day skating by the rare pro borne from this era (who hasn't overhauled approach multiple times) is oddly reminiscent of Clear Channel's "Alternative Station" heard inside a 2015 Taco Bell® dining room. While the pants have changed, the music hasn't.
Gen Two is the emotional group (that probably listened to Emo) which may still believe in a rollerblading future based on a strange mix of skateboarding and baseball marketing models. Considered "old" by most of Gen Three and all of Gen Four.
GEN III - MILLENIAL BRINKERS : 1998+
This lot have no idea what a wondergrind is (was). "TJ Weber who? What's a Bauer Box?" Have always thought of inline videography in unitary "sections" or "parts"- not "videos". Fastslide has always implied a balanced trick: not a terrifying two-stair tap. EMAGDNIM means a lot while Medium doesn't. Most likely started aggressing on skates mountain dewd for extremity and not simply recreation. This group only exists because of Disney's stake in ESPN Extreme Games marketing: they needed to pump new parental spending lifeblood into a slipping cash cow.
Gen Three have all become adults over the past several years, and so Gen I/IIs frequently make the incorrect assumption that Gen III share all historical domain knowledge based on relative age alone, although the divide can be fairly wide and deep.
GEN IV - THIS ISN'T FUNNY: 2005+
Unquestionably never bought a pair of grindplates with serious or practical intent.
Does not grasp the irony of Roces' absurdly successful Majestic Twelve continuous remarketing campaign and doesn't care to.
Gens II (and Gen I remainder, if not rounded out of the stats at this point) are baffled that someone so young is rollerblading at all. To be clear, many silently wonder if this segment's interest in rollersliding is actually part of a drawn out, deepcover Thrasher fruitbashing feature.
GEN V - AGGRESSIVE INLINE SKOOTING : 2012+
The seven year wave that elected to tripwhip rather than toeroll. Powerful rollerblading bosses in smoke-filled rooms the world over are scrambling for ideas to climb out of today's sales crater, while others lucked out and profited immensely by creating high quality trademarks. There are as few upstart rollerbladers from this era as are remaining from Gen Zero (none, basically).
I hope you found this unfair assignment of stereotyped nostalgia-laden tropes to be accurate and insightful.