Old Hollywood Starlets: 14 portraits in acrylic of striking actresses that are to die for

Painting people can be a massive pain in the ass.

I mean, you just get one thing a bit off and it looks like a completely different person.

I decided, once and for all, that it was time to get better at drawing people.

Doing it in colour scared me, so I did it in monochrome.

Back in 2018 when I started drawing on the iPad I wanted to learn how to use Procreate (my drawing app) better.

On canvas I’ve mostly painted in oil and I’ve used some acrylics over the years.

My favourite style of painting and drawing is highly realistic but with some abstract elements.

Usually, this means that I’ll paint like the eye sees – an area that is in sharp focus (in these portraits it’s the face) and a more blurred area around that (hair/decolletage).

Typically, the background would also be completely blurry – or even bokeh – but in these paintings I wanted to maintain a monochrome palette with minimal distractions in the background, so they’re all a solid colour.

The backgrounds do, however, change depending on the hues present in the photographs I used as reference for these paintings.

This gives each one a distinct look and feel.

I was never good at drawing humans

Truthfully, I’ve never been any good at drawing humans, so I’ve avoided it for most of my life.

It’s the most frustrating thing when you try to reproduce the exact look of a person but the eyes just won’t sit right and they look a little stupid.

Or the ears are the wrong shape and look out of proportion with each other.

Or the nose just isn’t turning out the right kind of crooked.

I’ve tried and failed many times – eventually settling on the much safer subject of horses, where I find proportions as easy to get right as walking on two feet.

But here, I decided, fuck it. I’m going to at least try.

I’ll give it my goddamn best effort and if it doesn’t work… well, I tried.

I went with old Hollywood glamour because I wanted a limited colour palette and chose black and white photos as reference material

I mean who doesn’t love that aesthetic?

Yes, it was a horrible time for women in the industry – for movie stars in general.

For some, the fight to transfer from silent movies to talkies never materialised, for others, it was a hard-won opportunity that came at a price.

Beauty standards were strict and a specific kind of beauty was appreciated and accepted.

And it’s easy to forget, that some of these women were actual real-life heroes in addition to just being famous for being on-screen.

Those are the stories that really fascinate me and what inspired me to choose classic Hollywood actresses for this series of portraits.

They’re in the order that they were painted – so that you can observe the progression of my learning (if there is any, lol!) – let me introduce you to the ladies.

1. Sophia Loren

So, my first choice was Sophia Loren.

Playful. Cheeky. Confident and sexy.

I felt safe with her – like I wouldn’t get berated even if it all went pear-shaped.

From Wikipedia: “Loren is an ardent fan of the football club S.S.C. Napoli. In May 2007, when the team was third in Serie B, she (then aged 72) told the Gazzetta dello Sport that she would do a striptease if the team won.”

The original photo was of very poor quality (very high contrast and a bit blurry) and I think it reflects in how flat the face looks because this painting is a true replica of the reference photo.

2. Jane Fonda

This is a photo of her in some kind of gown (hence the neckline) and I just adore that fiery look in her eyes.

I also wanted to refine shadows (especially the one falling across her forehead) because I’d struggled to make it look good in the first painting.

The face is less flat, though the hair was a challenge.

3. Audrey Hepburn

I wanted to keep it simple, almost austere.

My favourite images of Hepburn are when she’s dancing ballet and her hair is tied back from her face.

I was also aggravated with making big, fluffy hair look realistic, so I overcorrected.

Still, I think this has that delicate air about it that is so iconically her.

4. Josephine Baker

My lineup could never be complete without Jo Baker.

Singer, dancer, civil rights activist, decorated WWII spy her energy is like no other’s.

The darker skin was challenging compared to the previous portraits and took me longer, but totally worth the effort.

In the reference photo, she was also leaning against some kind of amphora so I had to make adjustments for that.

5. Bette Davis

The firecracker herself.

Known for her forceful and intense acting style she always loved to play the villains.

This is from a reference photo of a very young Davis, but with a career spanning 60 years she kept going until the end of the 80s.

The one sided hair was a challenge and the face isn’t symmetrical – though neither was she.

The shadows crossing under her chin were an experiment but in the end I was able to replicate the multiple-source lighting in the original reference photo.

6. Marilyn Monroe

I was attracted to this one because she isn’t’ looking into the camera and her eyes were still reflecting the set lights.

This also looks more like a candid moment, giving us a hint of the pain that was lurking under the surface.

The most popular photos of her tend to be the ones where she’s toying with the camera and has a big smile on her face.

I wanted to explore a different side of her.

The lips were difficult, the reference photo blurry at best (hence this is kind of blurry as well) and it’s a bit flat in places.

But it’s her, you can see it’s Marilyn. Though her signature hair looks more horsehair than it should!

7. Janet Leigh

Here I even surprised myself with how well I managed to nail that harsh light on the contour of her profile.

That’s the detail that really makes this portrait.

I spent a lot of time on the mouth getting the lips and teeth just right, which was well worth all the pain.

She’s looking shiny in the face, but that is, again, replicated pretty closely from the reference photo.

I really do love how that shine on the cheek and the laughter lines turned out.

One of my favourites in terms of technical execution.

8. Elizabeth Taylor

Yeah, don’t even talk to me about those teeth!

I was so focused on accurately replicating tones when I should have been paying more attention to the overall look.

This one got over-worked and lost depth on the nose – though I love how the eyes turned out.

And that long shadow from her eyelashes!

9. Ava Gardener

I think hands down my favourite one of the bunch.

She’s serving attitude, unrealistically long eyelashes, big hair and that slightly arched eyebrow saying, “Really? You sure about that?”

The backlit hair was difficult to get right, and the shadow on her forehead could have been done better.

But I love the shadow her hair casts on her forehead – makes you see just how big of a do it really was.

10. Hedy Lamarr

Hedy Lamarr I just love, her story is so tragic.

I’m glad that in the end, she got the recognition she deserved for co-inventing the radio guidance system for Allied torpedos that, today, is the basis for Bluetooth and WiFi.

From her supposed night-time escape, dressed as the maid, from her oppressive husband who just wanted a trophy wife, to the scandals surrounding her personal life, tragedy seemed to follow her throughout her life.

This portrait with the dark hair and lips to match, has that silent film feeling to it.

Looking off into the distance usually gives portraits a feeling of power and hope, but her submissive stance and looking up at something above her gives a feeling of submitting to fate.

Though the lips look a bit flat (they’re so dark) this is some of the best work with teeth I’ve ever managed (a small detail that’s easily overlooked, until I pointed it out!).

The hair also reflects less light than in the other portraits, almost as if it’s swallowing the light and creating a nimbus that, on the one hand, makes her stand out but, on the other, makes it seem like an air of gloom is always with her.

Her tragedy, of course, was that she was titled the most beautiful woman in the world and praised for her beauty while completely overlooked for how intelligent she was (she was an inventor in her spare time).

11. Carole Lombard

The highest paid star in Hollywood in the 1930s – for that to be a woman is saying something.

The blonde hair and light coloured eyes just make an incredibly captivating portrait in black and white.

The only word I have for it is ‘haunting’.

The strong above-head light casts some very harsh shadows but this time I’m really happy with how the shadows turned out.

The razor-thin eyebrows and tiny pinprick of light give her a piercing look, like she’s committing you to memory so she can come back and haunt you.

12. Ginger Rogers

From Broadway to Hollywood icon, Ginger Rogers is one of the reasons I started tap dancing.

Usually upbeat and with a big smile on stage, I wanted a more serious look for the portrait.

My favourite thing about this portrait are the piercing eyes and that hair, it looks like this perfect 1940s hair with poofy bends and so, so shiny.

Realistic? No. But fancy af. (And my reference photo was a very staged one, as pictures of this time tended to be.)

13. Lucille Ball

My other favourite of the bunch; Lucy was a goofball on screen, but a pioneer both in comedy and behind the scenes.

After starting on Broadway she eventually did I Love Lucy, one of the most-loved TV shows in history.

She’s been dubbed the Queen of the Golden Age, and she set new standards for television comedy and paved the way for women in her industry.

She was also a successful businesswoman who started a company that would go on to produce projects like Star Trek (which everyone else turned down).

I wanted a portrait that reflected her for the person she was, rather than the character she’s so loved for.

Gazing up to the right gives it that that hopeful feeling as she’s looking up and into the future.

I love this one because it almost feels like you’re looking at her rather than a painting of her.

And that’s the ultimate goal of a portrait, isn’t it?

14. Marlene Dietrich

She’s an icon for stage performers everywhere and patron saint of the opinionated!

She was named the ninth greatest female star of classic Hollywood cinema and her career was exceptionally long, from the 1910s to the 1980s – one of those who managed to move from silent film to the talkies.

She was also known for her humanitarian efforts during WWII – among other things she put her entire salary for Knight Without Armor ($450,000 at the time) into escrow to help refugees in 1937.

She continually reinvented herself over the decades and is still revered today.

I chose the reference photos because of those impossibly long lashes – nothing less can do justice to this woman.

The lashes (though it took a few tries to get it right) and their shadows add depth and intrigue to the look in her eyes.

So, was there any progression in technique? Composition?

I think I see some and, as I said before, maybe the Ava Gardener portrait is the one where it all comes together.