I often see Aston Barrett (and reggae in general) mentioned as an example of playing behind the beat but I think that this is a misconception that people have because they perceive reggae as chill / laid back music. Aston Barrett tends to play on the beat in my opinion and other famous reggae bassists do as well.
The other reason why reggae is perceived that way is because often the drummer will be playing a groove that implies swung eights but the eight notes that the bass player plays will be straight or at least not have the same amount of what in musicology is known as "swing ratio". Here's an example of that feel:
Great question! This has been a topic of many scientific researches. There are many studies where micro-timing (playing behind / in front of the bit is a part of that big topic) was researched any there are no clear answers. There are some studies that suggest that listeners perception of "swing" or "groove" was lower when micro-timing deviations were introduced. Meaning that they thought the music didn't swing when musicians played behind or in front.
I interviewed 3 renowned jazz musicians as a part of my bachelor thesis. One of them, a double bass player who plays with with the likes of WDR Big Band and Joey DeFrancesco was of the opinion that for the music to swing (when playing jazz music) the bass should be playing in front slightly, especially if it's a double bass since the attack of the double bass is slower than that of the electric bass.
Another very undervalued aspect is the actual length of the notes. Let's say that you're playing a walking bass line and all of your notes are 100% on the money each time every time. If the length of the note is inconsistent, the bass line is not going to swing.
People often have decent timing but lousy technique so position change or string skipping might cause inconsistency in note length.