This 1978 debut R&B/smooth jazz song by one-hit wonder (at least it's his only song with a Wikipedia article) blue-eyed soul singer (yes, he's white to the surprise of many) Bobby Caldwell started bubbling up as a meme mid last year for its opening few lines, mostly the first: "I guess you wonder where I've been".
On November 20, 2015 (before it was a meme), a "slowed and chopped" edit with an animated loop of a car driving at night (clearly going for a vaporwave/synthwave aesthetic) was posted by Nicolas Taiclet and has over 3 million views.
A less viewed but still popular (230k) YouTube video posted on August 11, 2017 by Wet Duck uses the same slowed audio and features a loop of Homer Simpson driving (Simpsonwave).
Another instance of this song before it became a meme is in this March 25, 2016 Source Filmmaker video with just under 70k views by YouTube user Gobsmacked Galaxy featuring Coach from Left 4 Dead 2.
A Google Trends search for the lyric "I guess you wonder where I've been" shows a sharp spike (literally 0 to 100) in July 2018. While I can't pinpoint its origin as a meme, it exists in the social spheres of Twitter, Instagram, and TikTok (and has spread secondhand to YouTube).
What may have kicked this off as a meme is a video of rapper Bobby Shmurda dancing from his "Hot Nigga" music video synced to the song (as part of what seems like a fad in which various songs are used). The earliest version (and I think original source, below) was posted to YouTube by AYYYBLAZERS on January 8, 2018 and has 57k views. I can't find a popular source, but it has since spread further in a cropped form (in length and frame) on Twitter/Instagram, presumably around July when the Google Trends spiked. I can assume this is a big part of the meme because "bobby shmurda" is high in search suggestions for the phrase and song title (both names being Bobby may or may not be an inspiration).
While the Shmurda video being spread in July is speculation, I'm pretty sure it was before August 21 as mashup artist toonlink (or Toon Link IRL) posted a mashup of "Hot Nigga" with the song on YouTube (43k views) and SoundCloud (21k plays).
On August 23, 2018 (2 days after the toonlink mashup), the most popular single upload I know of (just under 700k views) was posted by YouTube user comacow02. It features a Volvo 240 jumping a ramp made of snow, the first line playing as it lands and the driver faces the camera.
About a month ago, the song began trending on TikTok in what came to be dubbed the "Your Period Challenge".