The Cheeky Monkeys of Pop (now with added Robbie)

The original cheeky monkey, or Monkee - rather amazingly Mickey Dolenz was closely associated with some actual monkeys, early in his career, as a character in Circus Boy

A hint of simian is definitely a bonus with this archetype but not essential. 

Ian Brown playing up to it, having fun with it with the Unfinished Monkey Business album

Although as covers go it's oddly sinister 

 

And then the original spur for this meditation, Lily Allen 

At a low televisual ebb recently so found ourselves watching From Riches to Rags on YouTube -  an ancient docu-reality thing on Lily and her sister's attempt to start a vintage clothing rental boutique - the concept: haute couture too expensive to buy, but you could grub up enough cash to wear it for one night of feeling like a star. 

Diverting enough stuff, mainly for the cheeky-monkey charm of Lily who really doesn't seem cut out for business. (Spoiler: neither of them were).

Most of the time on camera, Lily's unmade-up and casually dressed - what I find disconcerting are the intermittent glimpses of her onstage or doing some kind of celeb-oriented event, paparazzi clustered around her as she totters on high heels, clad in a couture gown and caked in cosmetics.  

Disconcerting because her true essence seems much more like the Artful Dodger reincarnated. 

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So who else is there? 

Steve Marriott? 

Well, he in fact played the Artful Dodger in Oliver! on the West End stage long before he was a Small Face

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William in comments point out a glaring and obvious omission

This Stones pastiche reminded me of the existence of Mick Jagger - who has a simian quality but I don't know if he's exactly a "cheeky monkey"

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Oooh - thought of another. 

Well, I don't know if "cheeky monkey" is the word exactly but Saffron in Republica has a sort of bouncy bratty energy - like an 8 year old in a romper room. 

You could probably point to punky precursors  - The Slits - but I like to think of "Ready To Go"  as the inauguration of a likeable lineage of unladylike pop - I'd almost say "ladette" -  like which would include Icona Pop's "I Love It" and Pink's "Coming Up" ("get this party started") and early Ke$ha .  Charlie xcx... 

Now I think of it, are The Spice Girls a whole pack of cheeky monkeys?  

Talking of unladylike pop / ladette-pop, clean forget about Lady Sovereign

Who in many ways is the template that Lily Allen was basing her thing, albeit not rapping but singing 

"Cheeky monkey" is very much something to do with a return to childhood.

Pre-sexual - in the case of the female artists, there's a bratty 9-year-old tomboy quality that cuts against or is at odds with whatever glamour they are otherwise attempting to put across

The girl-gang comes first, coupling is a distant second

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Update August 9

Genuinely abashed to have missed one of those "standing in plain view" examples. 

It took Andrew Parker to point out the bleedin' obvious: 

Robbie Williams

He only made an autobiopic earlier this year in which he appears in the form of a chimpanzee 

Robbie Williams: "I've been a cheeky monkey all my life" 

More than a faint resemblance to Norman Wisdom, who had a simian aspect, as well as seeming like a perpetual 10 year old with a catapult pulled from the pages of the Beano or Just William

Norman Wisdom also had a pop career, singing glutinous chart-topping ballads that generally played on his image as the Fool, but extended that into amorous metaphors (fool for your love, you made me your fool, that kind of thing).

I have not seen the Better Man movie - well, I tried to watch it but had to stop after 10 minutes -  but did sit through a whole long (two-part I think) doc on Robbie. 

The gist of was that he achieved fame and public affection as someone for whom it was all just a lark, someone essentially paid to enjoy himself in public....  

But then he decided he wanted to be taken seriously -  he craved artistic credibility, wanted to say profound things and push the pop envelope, desperately desired to be "cool"... and this misguided ambition and consequent inevitable shortfall with attendant lashings of critical derision, tabloid mockery etc - this had him spiraling into mental fragility and addictive behaviours (I remember reading at the time that he was addicted to espressos and cigarettes, he would drink several espressos an hour while chain smoking - I expect this was just the lighter end of his issues).... 

And then at his lowest ebb, there was some kind of eureka moment. Robbie realised that some people just aren't cut out for depth.  They skate along the surface of life and there's nothing wrong with that. He realised that there wasn't anything more to him than being a born entertainer - a singing and smiling showman. So he went back to his true calling, effectively cabaret at arena scale - singing his most fondly remembered songs, giving it 110 percent onstage, putting on a grand show and taking people's minds off their own problems. 

Strangely during his dark, off-course days, his great aspirational idea of "deep" and cool was Oasis.

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Some cheeky monkeys of my own