Penny Lane and the Tyranny of Cool

In a heroes-and-villains culture, she fights for nuance — even if it’s a ‘dirty word’

The filmmaker Penny Lane will never be accused of being too cool, and she’s just fine with that.

“I feel tyrannized by the idea of being cool. The idea of being cool is the least creatively conducive concern you could have,” she told me on Rushfield Lunch this week.

A graduate of Vassar College who has taught film, video and new media art at Colgate University, Bard College, Williams College and my own alma mater, Hampshire College (which came up in our chat), Lane has always marched to her own beat. This is especially true in her films Listening to Kenny G (about the musician Kenny G) and Happy and You Know It (about artists who perform kids’ music), both part of the HBO documentary films series Music Box created by Bill Simmons.

“I started making films in a nonprofit job, helping 5-year-olds learn how to use video cameras,” she said. “I feel like I’m constantly having to put myself in the mindset of a little kid who’s just picked up a camera for the first time because that’s the only place I can be creative. It’s tough to try to do things and worry about whether people will like them, think they're cool or find them award-worthy. It’s a type of self-consciousness that is crushing.”

Lane hasn’t just made movies about music, of course. She’s also one of the great humanists, finding empathy in such subjects as the Satanic Temple (Hail Satan?) and the presidency of Richard Nixon (Our Nixon).

As a filmmaker, “I allow myself to feel empathy for people that I think in real life I would have a hard time feeling empathy for,” she said, an approach that sometimes runs her afoul of ideologues on either end of the political spectrum.

“Thinking of heroes and villains, I just don’t see the world that way. So my films never present the world that way,” she said. “It’s sometimes tough to occupy that nuance. I’m not making excuses for bad people, I promise…. But I think most audiences appreciate this kind of more humane nuance.

“I’ve got to find a new word other than nuance, though,” she added, “because I have been told that it’s coded badly now. I just don’t know what word to use.”

Watch our full conversation above for a further audit on the term “nuance” and much more from the delightful Lane, who is also a must-read on Substack at Penny Lane Is My Real Name (and yes, it is her real name).