Painting for Leo DiCaprio


I’m painting for Leo DiCaprio.

I can call him Leo. I read an interview (or ten thousand) with him. He says Leo is okay.

Perhaps you think it’s a metaphor.

Like I’m “painting for Leo DiCaprio“….. wink wink.

But no, I’m actually painting for Leo D.

I’m painting Leo a beautiful girl. One of my favorite girls.


And I know someone who knows someone who can find someone who knows how to deliver the painting to Leo D.

When I began painting seriously (i.e., obsessively but sans talent or training) a few years ago, something told me to send a painting to Leo D.  Something told me he would like my paintings.

Because he loves art.

And because he loves beautiful women.

I like Leo DiCaprio.

You might be thinking I’m obsessed with him, but I’m not.

I think he’s gorgeous. And I think he’s ridiculously talented. And I like that he appears to be pretty cool in real life and not too into himself.

But I’m not obsessed with Leo D. or in love with him.

Well, maybe I am just a little.

But I swear I just really think he would like my paintings. Something in me says he would like them as much as I do.

And here’s the thing….I need to move to the next level with painting if I’m going to be able to paint more.  I need to start showing paintings or selling paintings or both.

And I really, really, really want to move to the next level.

There. I said it out loud.

I really want to do more with painting and less with my day job.

Leo DiCaprio was in one of my all time favorite movies, What’s Eating Gilbert Grape.

WEGG came out in the spring of 1994, which means I would have seen it in the spring of 1994.

In the 1990’s and the two previous decades, I waited for movies like people wait for mail.  I paced and anticipated and counted the minutes and then obsessed for hours and days about what had been delivered.

I was a bit of a movie snob back then, limiting my movies to foreign or at least mildly confusing or deep American films.

So Gilbert Grape was right up my alley.

Gilbert Grape was deep and dark and real and raw.

Even better, Gilbert Grape dealt with disability and mental illness.

I LOVED disability and mental illness back then.

I still love disability and mental illness. I just do a better job of balancing those passions more better with my other passions.

In 1994, I had just started my law practice.  I was focused on all things related to the Americans with Disabilities Act and I was intent on forcing the world to think about disability issues.

I was angry and frustrated and inspired and hopeful and I knew what I was doing was important.

Now I just want to paint.

And write.

And make funny cartoons.

And, if I can, I’d like to help someone avoid some of the pain I lived.

Because it took me way too long to learn how to live with pain.

So I fantasize about giving a painting to Leo DiCaprio.

And Leo gets the painting and loves it.

And he buys another painting or two from me.

And then he says, “Did you always want to be a painter?”

And I say, “No, Leo. Actually, I really just wanted to die. Because I have a messed up brain that feeds me bad messages. But I kept working and focusing and I stayed independent and now I’m ready to trade all of that for painting. First work kept me from making plans to die and now painting keeps me from making plans to die.  See how helpful the arts are to those living with challenges? Everyone needs to support the arts….for those art saves.

And Leo says, “You know, I’ve played a host of characters living with challenges.”

And I smile and say, “I know, Leo. Playing characters living with challenges helps those living with the actual challenges. You have no idea how much, but I do.  It’s really important to show the world those charactersand to help the world understand that living with challenges is just another way of living.”

And then I add, “You should know that What’s Eating Gilbert Grape really helped me. It came out at a time when I needed something to help me get by.  It helped me get by.”

And Leo blushes because he’s pretty humble.

And he says “You know, I just played that character. I’m not really challenged.”

And I say “Yes, but you cared enough about the part to live in that character and learn to understand that character. And then you shared that character with lots of people who hopefully saw a bit of themselves or their son or their neighbor in your portrayal.  Hopefully they connected with the character and realized how human the character was. Hopefully they saw that the character was living with a challenge…not just beating a challenge. You can’t beat every challenge.

And Leo says “You can do that with your paintings. You can share your characters with others who need to connect.”

And then I let Leo it was his idea.


Speaking of sharing stories, I’ve been watching I Am Jazz with my nieces.

It’s a must watch. For everyone.


It’s well done.

And it’s important in many, many ways.

And it’s heartwarming. And heart hurting. And sweet. And personal. And relatable.

It’s everything, just like life.

Okay, back to work everyone.

Happy Monday. Or something like that.

xoxo, d




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