These particular bad boys lurk in the closets of slang. No more than a small gang of inverts and perverts with senses that come out arse-about-face. Perhaps that should be ‘ass’ as the non-ironic origins of most, if not all, are in America.

Once an adjective has been hijacked, positives and negatives hotwired and reversed, the result can give a powerful charge to the wordplay of rap and hip-hop culture. However, you might be surprised to discover that one or two of these inverted senses have been around for a good deal longer than you.


Meaning ‘good’, turns up at the end of the nineteenth century and is still with us.


George Ade, Pink Marsh, 1897

In the 1980s hip-hop got bad and bad got hip, nuanced now as somewhere on the ‘cool’ pop spectrum between awesome and excellent.


You know I’m smooth, I’m bad, you know it.

Michael Jackson, Bad, 1987


Never retire or put my mike on the shelf

The baddest rapper in the history of rap itself

Not bitter or mad just provin’ I’m bad

You want a hit give me a hour plus a pen and a pad.

LL Cool J, I’m Bad 1987


Tim Westwood/BBC Open Space, Bad Means Good, 1987


Not bad meaning bad, but bad meaning good good good.

Drake, Bad Meaning Good, 2006



It is argued by some that gay is now such a positive word that its use as a negative is a natural evolution. Others contend that use of gay in a negative context is unquestionably homophobic. Historically, gay has a wealth of meanings – but that’s a whole nother conversation. The poor, bad, lame sense that sits nicely in this list originates in American English in the late-1970s.


‘Aw, man! You kissed a girl.’

‘That is so gay!’

Mike Scully, The Simpsons: Lisa’s Date with Destiny, 1996



‘You mean the guys in that Prince movie?’

‘Yeah, “Purple Rain.”’

‘That shit was so gay.’

‘Fucking 80’s style.’

Kevin Smith, Jay and Silent Bob Strike Back, 2001



From the mid-1980s into the ’90s and still going in the noughties. Good, great or sexy. Verbified for being ‘awesome’, excellent or sexy.


Most illingest b-boy – I got that feeling

Cause I am most ill and I’m rhymin’ and stealin’

Beastie Boys, Rhymin & Stealin, 1986


No one, no one is iller than me. No one is iller than me.

Eminem, No One’s Iller, 1998


What’s up yo, cool man chilling,

I’m dealing with this girl, yo man she’s illing.

Manafest, Manafesto, 2005



Meaning very good, excellent, shows up in the US in 1983 (according to the OED). These UK examples are later.


She’s so sick like a dope melody sittin’ nicely on top of the beat.

 Craig David, Kinda Girl For Me, 2007


Snoop gave it some thought. ‘Nathan they like. They think he’s well-sick. But the other one? Jacob. His face don’t fit so well.’

Alex Scarrow, Afterlight, 2010


the shit

The definite article is unavoidable. This is the best. The OED records its earliest use in American College Campus slang in 1987. The first quote below, also US, is going on 20 years earlier.


I beat it on a single quarter regularly. That’s pretty good. You know what system is rad? The Vuctrux. That was the shit. It was bigger in Urope though. I got to play it once. Vectur graphics are just really cool.

Nathan Smithe, The Bible 2.0, 1969



“The Head loved poetry, he thought that stuff was the shit. He was…” Jordan’s voice, which had been strangely gay all night, finally broke. “He was totally so totally old-school.”

Stephen King, Cell, 2006

Cause I’m the shit
Yeah I’m the shit
Up in this bitch
Up in this bitch
Yeah I’m the shit
Yeah I’m the shit
Up in this bitch
Up in this bitch

D. J. Class featuring Kanye West, I’m the Shit, 2009


In this sense it has been found as far back as 1920. Yes, America again. Yes, 1920.


“Tell ‘em to play ‘Admiration’!” shouted Sloane. “You two order; Pheoebe and I are going to shake a wicked calf,” and they sailed off in the muddled crowd.

F. Scott Fitzgerald, This Side of Paradise, 1920

Now wicked bestrides the Atlantic as a stand alone adjective and, mainly in the US, stands by to intensify awesome and cool. But it’s no longer as cool and awesome as it thinks it is.


“Wicked! Well wicked!” Sophie cried, crossing her legs awkwardly and nearly knocking her pint over.

John Phillipson, Bright Lights, Summer in the City, 2009



For my husband, Jesse, who is wicked awesome.

Suzanne Young, dedication, A Want So Wicked, 2012



He had his first lesson yesterday and absolutely loved it. Snowboarding is the coolest, and I was pronounced the coolest mom ever for letting him become a wicked cool snowboarder.

Lisa Genova, Left Neglected, 2011


There are, of course, other words that carry a sense at odds with their etymology but each and every one of the positive-to-negative words listed here is remarkable. Not one of them waited for evolution. Each came about by terrific and immediate reversal (or spanking perversion) of a conventional or contemporary sense.

How awfully bad is that?