I started playing 5 around 1988, a little while after Whitney Houston's first album came out. Nathan East was arguably the first guy to play 5 string bass on a big pop hit, and it was all over the radio and hard to ignore.
Heard "Saving All my Love for You" and I had to have that sound. Of course, the internet had yet to be invented, so I asked everybody I knew because I didn't know how Nate got those notes below "E". This took some time to get figured out - bear in mind it was 1988 and 5 string basses were something most players and music retailers didn't know about. They were already out there, but very rare and almost always built custom by small luthiers. Most of the older players didn't know who or what Nathan was, some said he tuned down, and then the premiere Gospel player in town told me it was a 5 string bass, with a low "B" string below the "E".
A short time later, he and I ordered Yamaha BB5000 models, like Nathan played at that time. He still has his, but I regret selling mine - that was a great bass.
Close to 20 years later, playing 5 is almost a requirement in a lot of styles of music. If I get called to a pick-up job where I'm not sure what tunes will be called, I'll play 5 string just to be covered if I need it. I still like playing 4, but I use a Hipshot on them.