He contradicts himself "on the regular"

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.

This thread is from July but I was just now looking up the phrase as it has exploded across my local demographic--middle aged white SF Bay Area folks-- in the last year or so. While some of us may be plugged into hip hop culture it seems like diffusion from younger people. Without knowledge of hip hop origins, it sounded to me pleasingly down home. Associated phrasing like "On the daily" is also heard, if less common.