He contradicts himself "on the regular"
This phrase was used to describe Donald Trump in an article in Salon magazine.
Donald Trump is a better politician than a lot of people give him credit for. Granted, he often has no idea what he’s talking about, he contradicts himself on the regular, he has a repellent personality, he’s a misogynist and a bigot, and it feels like he stumbled ass-backwards into the Republican presidential nomination.
- Salon
According to multiple slang dictionaries, including Online Slang Dictionary, "on the regular" is well-established slang for "often," "frequently," or "routinely." It is mainstream enough to be found in reputable print journalism (see below for that).
regularly; frequently. Also on the reg.
Ex: I hit up that spot on the regular.
- Online Slang Dictionary
Searching Ngram isn't very useful for this question because the phrase can be part of typically grammatical sentences, like "It wasn't on the regular menu."
Most of the anecdotal uses that I've been able to find have been within the last year or two, but I expect that it must have been a slang expression for longer than that in order to show up in the likes of Esquire and Rolling Stone.
Questions:
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When did this phrase come into vogue?
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Is it uniquely American slang, and did it originate with a specific region or culture?
To vouch for the legitimacy of this phrase and prove that this is a serious question, here are few uses from major print publications:
Although it's damn near impossible to wake up flawless like Beyoncé on the regular, it is possible to get pro concealing tips from her makeup artist
- Cosmopolitan (2017)
It doesn't matter whether you and your buddy from work go out for drinks on the regular and play on the same intramural co-ed after-work bowling team: You still shouldn't trust them to keep your secrets.
- Esquire (2017)
Understanding West Virginia has taken on a newfound relevance since the aftermath of the most recent Presidential election. The state has occupied an unlikely place at the center of American politics so far this century, inspiring thinkpieces on the regular every four years.
- Rolling Stone (2017)
Okay, so I've done some additional research and I've found even earlier usages of the phrase, on the regular.
The rapper "Defari" on his album, The Next Chapter, in 1995, on the song "Big Up" has this verse:
Link to Defari lyrics for the Big Up song
Verse 3: Lyrics are gold plus steel for the raw deal
Feel MC's and DJ's nuff respect y'all real
Low caps I rock on the regular
Brim covers my eyes so ducks can't see their predator
Facefirst when I disperse yet another verse
INTERESTING NOTE:
You can see how he is using the phrase in line 3 to rhyme with line 4, "see their predator".
ADDITIONAL FINDINGS
In 1996 there was a compilation album released by Interscope Records called Insomnia. It included a song called, On The Regular, by Duo. That song has various verses with the phrase: on the regular
HYPOTHESIS
I do remember hearing this term around the early to mid 90's in the US. I was around 20 or so at the time. Of course it's possible that it was used earlier than this but I think it's highly likely that it started around this time, with songs like these, as a result of trying to rhyme words in rap songs.
It's important to note that it became very common, and is even more so to this day, especially in African American and hip hop/rap culture, to create new phraseology and euphemisms. For one it helps create an identity (which is something the early rap culture - especially in the US - really wanted badly) along with the added value of allowing you to rhyme songs that would otherwise be nonsensical.
My position is that this is how we have come about many of the colloquialisms of today. This on the regular phrase is one but there are many, things like: "throw up a deuce" (to show a "peace" symbol), "roll a fatty (or blunt)" (talking about smoking pot), bling (jewelry), rims or 20's (nice wheels on a car), "gimme a 40" (pronounced "foe-tee") to mean 40oz beer (it was common in the "hood" or ghetto for people to buy 40oz alcoholic beverages). There are tons of these types of words and phrases and many variations. "I'm out" (leaving) comes from rap's early "Audi 5000 G", which just meant, "I'm outta hear guys". Audi 5000 was a popular and desired car by that culture at the time. It eventually morphed to simply "Audi" and then finally "out" or "outta" or "outtie".
FINAL THOUGHTS
So, basically, these words are a way to create identity within subcultures and they are also the mechanism to create rhymes for songs.
I would peg the origin of this particular phrase at around 1990-1995, probably occurring on the west coast and/or southern parts of the United States. Defari was a west coast [California] rapper at the time.
The first use I can identify is from Dr. Dre's 1999 track Xxplosive on the album "2001":
Pimping bitches on the regular, I put that on the G
A hustler and a player, nowadays it pays to be
I can personally attest to having first heard this in use between 1999 and 2003 in the form of "hooking up on the reg". This was from white American musicians on the West Coast (Portland, Ore.) heavily influenced by hip-hop artists including Dr. Dre and Snoop Dogg.