It doesn’t take much to get a story out of Leonard “Boogie” Weinglass. Just walk through the front door of his house on McClain Flats and this Aspen Hall of Famer, born in 1941, will start telling you about the women he’s loved, the fights he’s won, and how in the early 1970s his fashion sense and business acumen bootstrapped a billion-dollar retail empire that dominated the industry for two decades. 

Once a scrappy kid from a poor Jewish family in Baltimore, Boogie—along with business partner Harold Goldsmith—would eventually oversee more than 1,400 Merry-Go-Round clothing stores. Boogie’s “Merry-Go-Ranch” property near Aspen, where he still spends much of his time, is larger than the entire neighborhood he grew up in. And his flagship Boogie’s Diner—a Planet Hollywood-style themed restaurant and retail hub on East Cooper Avenue—once blamed for the “Boogification of Aspen” now inspires more nostalgia than scorn.

“I think it was the last true center of community in Aspen,” says Greg Lewis, an Emmy Award–winning journalist and local writer whose book Boogie: Afraid of Nothing Except Being Nothing was published in 2025 (available locally at Carl’s Pharmacy and Explore Booksellers, and online at borderlandspress.com). Boogie, sitting opposite his biographer in the living room of his Merry-Go-Ranch home, concurs. At its peak, Boogie’s Diner, which Lewis describes as an “egalitarian” joint, served 1,200 customers a day, treating locals like celebrities and celebrities like the average Joe. 

“Boogie took care of everybody,” Lewis says. “There is no place like that in Aspen anymore.”

And there aren’t many people like Boogie almost anywhere but here. He’ll tell you that he once stole a cop car and that he slugged a guy for muttering an anti-Semitic slur. No need to ask about the time he walked into an all-Black boxing gym to train; he’ll tell you about it anyway. His hair has gone white and is thinning, but the subject of the ponytail he used to wear still comes up a lot. As does his prowess on the basketball court and the dance floor. (How did you think he got the nickname Boogie, after all?)

All this, and more, is part of the Boogie biography, an expressive 250-odd pages that took Lewis some four years to complete. It’s based on hundreds of hours of interviews and a “methodical” writing process that captures Boogie’s life with a rhythm and groove that fits the subject. 

Others have told Boogie’s story too, via scores of magazine profiles and newspaper features, another biography, and a film—Barry Levinson’s Diner starred Mickey Rourke as Boogie. But according to Boogie, this version by Lewis blows away all those other accounts.

It’s “the best,” Boogie says. “It really is the best.”

“I wanted people to understand where he came from and what drove him to get out” of Baltimore, Lewis says. But, also, “his self confidence, his drive, ambition and work ethic, and courage—frankly, maybe, courage with a little bit of naivete mixed in, because when he got an idea to do something, he just did it.”

For all the money Boogie’s made, he’s given a lot of it away—and not only because he has a history of high-dollar gambling. His namesake Aspen diner closed and sold for $27.5 million in 2015, after a nearly three-decade run on the corner of Cooper and Galena, but his name is still attached to the Boogie’s Buddy Race that fundraises for the nonprofit Buddy Program’s youth mentorship in the Roaring Fork Valley; he and his wife, Gail, also host the annual Bash for the Buddies. He’s been known to bankroll medical bills for community members in need, tip $50 when $20 would have been generous, quietly look out for the little guy, and stick up for him when the moment calls. 

As described in Lewis’s book: Boogie is a “raconteur, philosopher, philanthropist, fighter, playboy, hero, star, salesman, lover of life, of women, of anyone in need.” 

An Aspenite, through and through.