Little By Little, Learn About Little Ricky Pt. 5

A pageboy bob, thick dark sunglasses, and a serious expression. As soon as you hear these words you automatically know who is being talked about, and that’s just what Dame Anna Wintour wants. The legendary Editor in Chief of Vogue since 1988 is untouchable to all around her, and the walls of her fashion palace have kept her regal persona away from the public to be admired from afar. Despite her best efforts to keep everyone at a distance, Little Ricky has come to form a unique connection to Wintour.

Little Ricky’s Anna Wintour SHEEP series contradicts the image that Wintour worked so hard to build for herself. It chips away at her standoffish image and gives you a fun, silly, and approachable figure who can laugh at the seriousness of her real-life counterpart. Little Ricky tells Sold Magazine:

“When I originally drew Anna back in 2018, I was simply re-doing a painting from a previous series featuring Naomi Campbell throwing cans of Campbells soup. In one scene in particular, Naomi is throwing soup cans at Anna. Once I put this scene together, various scenarios started popping up with Anna in silly situations. They made me laugh. Toward the end of the year, I realized that I had 'something' and eventually committed to doing a year-long project featuring Anna.

I didn't want to over think it; I wanted to let it flow organically. I knew that simply by painting her as a pink sheep, I was stripping away the serious personae that she's known for. Anna as SHEEP is pure silliness; I wanted to enjoy the simplicity of it. I knew that if I just let it run its course, something more would come from it and surprise me. It did!”

While the series began comically, it has since evolved into a something meaningful that connects Little Ricky to this elusive icon in a profound way. For Little Ricky, the Anna Wintour SHEEP series freed him from overthinking his actions, art, and way of thinking. Wintour has unknowingly helped him break free of the social judgements around him and take control of himself and his inner Wintour.

“Two months ago, I received an Instagram direct message from a close friend painting a negative picture of her (Anna Wintour). I let it go for a bit but knew that I had to think about it. Other than finding humor in the scenes that I was placing her in, I wondered, what exactly about Anna drew me to her? When I sat down for a bit and thought about it, I had a light bulb moment.

Painting Anna as a pink sheep and stripping away all her seriousness was a reflection of my own journey in life. Since starting the series in 2013, SHEEP has allowed me to break down whatever barriers I had left. It forced me to look at myself as a public persona, in the same way Wintour does. For most of my life, I've made it a point to be alone, to have my 'ME' time. I know I've been selfish that way. With SHEEP, I'm freed to live my life with open arms... I get to live from a vulnerable and magical place knowing that I'm doing exactly what I was meant to do. It's like I now belong to the world and 'ME' time is the last of my worries. I never imagined that I'd come to meet and know all these incredible humans simply by working on SHEEP and creating expressions of 'sheep' joy! There's no going back and it all feels F*king amazing!"

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Just another "Little" bit about Little Ricky, in order to get to know him better! Be sure to check out the entire series, and more to come leading up to a BIG show this FALL!