By the end of 2015, Aaron Ross had grown somewhat tired of playing Aaron Ross. The creator and host of late-night talk show pastiche Who's the Ross had honed his nightclub Letterman schtick through 600-plus performances in nine years—the first five as "boozy, polyester-clad inspirational speaker" Ed Forman—but hoped to find his own voice by launching a new series. Training Wheels, the web sitcom whose first season concluded this December, stars Ross as a frustrated live talk-show host named Aaron Ross.

"In some weird way," Ross says, "this was a more honest outlet."

Joining forces with a director he'd met while filming shorts at Pickathon, the bare-bones production team shot a 20-minute pilot in December 2015 and finished another three episodes the following year. Given their minimal resources, the first few installments of Training Wheels reflect their lead's daunting ambitions, but they're not always the smoothest ride. Ross and Wheels co-creator Jordan Paladino, an unsinkable luckless sidekick still living with his mother, trade wearying banter—the tone lurches from stoner absurdism to dry cleverness—amid premises that can be oversold. With a titular metaphor already somewhat trite, did they have to shove Paladino on actual training wheels?

And yet that cycling bit (and subsequent meet-cute with an attractive passer-by) leads into a sparkling medley of quick-cut, first-date moments highlighting Paladino's adorably hapless flirtations around Laurelhurst Park accompanied by an acoustic "Wouldn't It Be Nice" from And And And frontman Nathan Baumgartner. Clunky construction and an unearned self-delight are sins of amateurism readily forgiven by the flourishes of comedic bliss gracing each episode. And the showrunners have a transcendent gift for montage. However creaky the setups or uneven the pacing, all anyone should remember from the "Dad" episode is the deft, gleeful scene in which Ross amuses himself at the hardware store via crackerjack gags set to a tune written for the scene by Who's the Ross bandleader Justin Chase and his Rare Diagram partner Emma Browne.

Though Training Wheels' creators had no professional experience in television production, Ross' other career engendered certain advantages: pre-existing relationships with local musicians, free rein at rock clubs and strip bars that would ordinarily charge thousands for location shoots, and a readymade fan base eager to crowdfund $10K-ish to finish the season. Filming five episodes in as many weeks the following spring, the showrunners' financial gain led to exponential leaps forward in production values while Ross' character received upgrades just as noticeable. Where early episodes depict an amorphous protagonist lurching between ill-matched poses, the second run finds "Aaron Ross" reborn as a rom-com everyman pitched somewhere between Ryan Gosling and Eddie Bracken, and the duller role lets Ross shine.

Training Wheels' 10th installment, which premiered Dec. 9, returns to the beginning as Ross attempts to film a pilot loosely based on his own experiences helming the live talk show. The creators very consciously intended the episode to function as either a suitable capstone or pathway forward, though superfans bingeing their way through all available offerings should expect any further chapters to depart significantly from what's come before.

The Portland native has since moved down to the city he insistently calls "Ross Angeles," but credits his hometown as playing an integral role in the series. Meanwhile, Paladino, Ross reports, "moved to a pizza place in Portland, still lives with mom, and still can't ride a bike." Should funding come together for a professionally funded remake of Training Wheels' debut run, he's plotted out future arcs but seems unlikely to crowdsource another micro-budgeted season or fold the story into a feature film.

"If I was to take on a movie," Ross says, "I would definitely not play myself."

SEE IT: Training Wheels can be seen at youtube.com/trainingwheels.