Richard Schenkman!

Welcome to a SPECIAL EDITION of the Piece of Advice Newsletter!

Good morning! Today we are looking into a very interesting director and his work, Richard Schenkman! I was even lucky enough to ask him a few questions!

Richard Schenkman’s career has been defined by curiosity; the kind that drives a filmmaker to explore the full range of human experience, from love and regret to immortality and redemption. Born in New York City, Schenkman began his creative life behind the camera long before his name appeared in movie credits. After graduating from Tufts University and studying film at NYU’s Tisch School of the Arts, he directed hundreds of music videos and commercials during the booming MTV era. That fast-paced, visually creative environment honed his storytelling instincts and set the stage for his leap into feature filmmaking.

His breakthrough came in 1996 with “The Pompatus of Love”, a sharp, talkative indie comedy starring Jon Cryer, Adrian Pasdar, and Tim Guinee. The film, inspired by a line from the Steve Miller Band song “The Joker,” followed four men navigating the mysteries of modern romance and communication. It became a quiet cult favorite for its authentic, conversational tone; a style that would later become one of Schenkman’s trademarks. He followed it with “Went to Coney Island on a Mission from God… Be Back by Five” (1998), a poignant, offbeat drama that again starred Cryer and showcased Schenkman’s ability to balance humor with deeply human emotion.

But it was “A Diva’s Christmas Carol” (2000) that brought Schenkman into the living rooms of millions. Tasked with reimagining Charles Dickens’ classic for a new generation, he cast Vanessa Williams as Ebony Scrooge, a glamorous, self-absorbed pop diva haunted by the ghosts of Christmas past, present, and future. Filmed in Toronto with a blend of wit, heart, and a wink at celebrity culture, the movie became an instant holiday favorite on VH1. Critics praised its clever modernization and Williams’ fierce performance, while viewers embraced it as a new holiday tradition. Schenkman’s direction struck the perfect tone; campy yet sincere, satirical yet moving;  capturing the spirit of redemption that makes Dickens’ tale timeless.

In the years since, Schenkman has continued to defy easy categorization. His film “The Man from Earth” (2007), based on a story by legendary sci-fi writer Jerome Bixby, became a word-of-mouth phenomenon for its audacious concept; a 14,000-year-old man revealing his secret to friends during a single evening conversation. It showed Schenkman’s gift for turning intimate dialogue into something profound. Whether reimagining holiday classics or probing philosophical questions about humanity, Richard Schenkman remains a storyteller unafraid to blend intelligence with emotion.

Bonus Questions:

Giancarlo: What was your favorite movie growing up?

Richard: This has always been an impossible question for me; when I see people on red carpets being questioned by Letterboxd, I always wonder, "How do you pick four favorites?" By the same token, I could never pick one, firstly because it changed all the time, and secondly, because I find it impossible to weigh films from totally different genres against each other.

Having said that, when I was very young, my favorite movies were probably musicals, like the Beatles' pictures "A Hard Day's Night" and "Help!", and several of the Fred Astaire/Ginger Rogers pictures from the 1930's. Of course "Singing in the Rain" was a favorite and still is (frankly it's the best musical of all time, period, and one of the best pictures of all time to boot). 

I was not much of a horror fan, but I saw "The Exorcist" upon its original release, and it scared the crap out of me. I loved the James Bond movies; the first one I saw was "You Only Live Twice," and then I made a concerted effort to see all the rest of them. Indeed, around the time "Live and Let Die" came out, I actually started the world's first James Bond 007 Fan Club, and published a magazine called "Bondage" for quite a few years.

Giancarlo: Did you have any push back from friends and family on wanting to be a filmmaker?

Richard: No. I was very lucky; even though I grew up in a suburban neighborhood with regular, middle-class professionals, there was a lot of creativity in the community. More importantly, my father owned a couple of dry cleaning stores in Manhattan, and two were in some of NYC's most creative-packed neighborhoods: the Upper West Side, and Greenwich Village. So he had customers who were writers, actors, directors, producers, novelists... some famous, and some not. And this was crucial: He saw first hand that even people who were not household names could make an excellent, rewarding living in the arts. So when I said that I wanted to be a filmmaker (writer/director), he knew that it was very possible to make a living at it, and so neither he nor my mother insisted on a more traditional path for me (doctor, lawyer, etc). I do have one regret, though... my father felt very strongly that I should pursue a career as a television writer, but I had my heart set on making feature films. Many times I have felt that if I had chosen the path he suggested, I would have had a much easier -- and much more lucrative -- time of it. But... here I am.

Giancarlo: Which of the films you worked on are you the most proud of?

Richard: Another tough question; I'm incredibly proud that so many people -- millions of them -- have seen and loved "The Man from Earth" and "A Diva's Christmas Carol," but my "best" film --- the one closest to my heart, and closest to the vision I had when my friend Jon Cryer and I wrote it together --- is "Went to Coney Island on a Mission from God... Be Back by Five." It breaks my heart that more people have not seen this picture. 

Giancarlo: What is your favorite aspect of “A Diva’s Christmas Carol”?

Richard: Well, you could mean my favorite aspect of the finished film, or my favorite aspect of the project as a whole. 

For the latter, I'd have to say I cannot narrow it down to one: making the film was sheer joy, partially because my then-pregnant wife came to join me in Montreal and we had a wonderful time together (it was probably the happiest time of our marriage), and partially because Vanessa was so wonderful to work with and I knew each day that we were making a good, solid movie.... I'm so, so happy that so many people love the movie and consider it part of their holiday traditions, and of course I'm deeply grateful that a true friendship with Vanessa grew from the experience; we've worked together several times since.

My favorite aspect of the movie itself is also multi-pronged: I'm proud that we were able to closely hew to Dickens' story and themes while utterly modernizing the setting; I'm proud of how funny and purely entertaining the picture is; and I love the music, both the original songs, and the incredible score by Christopher Lennertz (who has gone on to be a hugely successful composer for film & TV).

Piece Of Advice:

Giancarlo: What is this best piece of advice you’ve ever been given?

Richard: This is one of those questions for which I should have a ready, brilliant answer, but while I love other peoples' answers to it, I haven't thought of my own. Of course there's the old standby, "Don't give up on your dreams," because you never know how long it's going to take until that break comes along, or "Say 'yes' to everything," because you never know what is the project, big or little, that's going to open up the magic door. But I think I'll offer two that my early career mentor gave me, one of which I (foolishly) ignored, and one I did my best to adopt... The former was, "Find people you admire or whom you'd love to work with, and take one of them to lunch every week. Ask them how you can help them -- don't ask them to help you -- and offer to work for free or do whatever it takes to spend time around them. This will lead to relationships, and eventually work." But when he gave me this advice, I was really at a low point, emotionally and financially, and the concept just felt overwhelming to me. But I should have done it. The latter was, "If you're too busy, you're not charging enough," and that was about as succinct and brilliant a piece of advice as I've ever heard.

Thank you for reading! Have an amazing day and we will catch you again soon!

-Giancarlo