Leonard "Len" Pickering is Amy Beckwith-Chilton's father, and was the editor in chief of City Limit magazine during much of the time the offices of this publication were the main location of the Bobbins strip.
In 1999, when Len was fired as editor for the first time (he was soon back again), he said he had been at City Limit for 33 years, meaning that he began working there around 1966. This overlaps with the time Bill Tweedy was said to be the editor in chief ('60s through '80s), so apparently Len held lower-level positions first. By 1992, he had received the promotion to editor, as his "Editor of the Year" award from this year shows.
Later, in 2001, he took a leave of absence (which proved to be permanent) due to "being a fruitloop" (in Bill's words), resulting in Bill becoming acting editor. Still later, Holly West became the final editor before the publication folded.
As editor, he tended to focus the magazine on things related to barnyard animals, which was perhaps not the best choice for achieving a hip, upscale demographic of readers. However, his successors didn't do any better than he did at reviving the fortunes of the publication, perhaps an impossible task given the general decline of print media, so he doesn't deserve all the blame for its failure.
After his career as editor, he later became a professor of journalism at the University of Tackleford, in which position he assigned Rachel Dukakis-Monteforte to re-establish the student newspaper, kicking off an adventure. Later on, Len was reported to be a dean at the university, but he's apparently retired now.
Did Shelley Meet Len First, or Amy? Edit
A continuity glitch between the original Bobbins strips and a New Bobbins strip has it unclear whether Shelley Winters met Len or Amy earliest. In one early strip, Amy (then the receptionist) tells Shelley that "the boss wants to see you" (for what turns out to be extracting his hand from a jar it is stuck in), and Shelley replies that "I've never seen him". (So apparently she got hired without an interview with him, and went the first few weeks or months of employment in a fairly small office without bumping into him.) However, a New Bobbins strip "retconned" into the same time period has Len bringing Amy into the office as the new receptionist and introducing her to Shelley. This clearly takes place earlier than the other strip in which Shelley has not yet met Len. Or maybe they just take place in different timelines altered due to time travel; this happens a lot in the Tackleford universe.
Len is notorious for going through numerous relationships, including a reported five ex-wives, and an unknown number of significant-others he didn't marry. However, the relationship shown with Shelley Winters (along with his superhero career shown at the same time) turned out to be a dream. Len's habit of going publicly naked every year seems also to have been a dream sequence.
His attempts to win the love of actress Drew Barrymore resulted in his organizing the Woo Drew variety show.
One of his many relationships was with Amy's mother, who has never been shown, but apparently has the surname Chilton. They seem to have separated after a fairly short relationship, and Amy lived with her mother until she was expelled from multiple schools, resulting in her mother dumping her on her father. Amy and her father still ended up with a good loving father/daughter relationship, with occasional contention where Len objected to Amy's financial irresponsibility (at one point cutting her off from his money and forcing her to earn a living on her own) or her tattoos (at one point she had tattoos removed to keep from being disinherited, though she later got even more tattoos anyway), while Amy often objected to Len's crazy antics and attempted to protect him from himself.
Len kept maintaining friendly relationships with several of his former employees, even long after their time at City Limit. Shelley included him in her Super Best Friends Society, founded by her in order get a few helping hands for the Super Crisis Quests. (The job entrusted to him by Shelley was "co-ordinating the war effort", which shows that Shelley was still having some faith in his leadership or administrative skills.) Likewise, he and Tim Jones continued to be on friendly terms. Ryan Beckwith once suspected that although Len was "jealous of Tim's lush hair", Tim provided "a vital gateway to the world of the quite young" for him. And speaking of Ryan - even though he had never worked for City Limit, Len apparently liked him too, considering how he was beaming with pride on Amy's wedding day, when Ryan became his son-in-law.
Len was also very fond of his guinea pig Cecil. Cecil could be seen in Bobbins and in the earliest years of Scary Go Round, but later ceased to appear, presumably due to the short lifespans of guinea pigs.