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Why play a fretless bass?

For certain styles, a fretless bass sometimes fits better sonically, e.g., folk, blues, Americana, most types of jazz, anything with lots of synthesizer in it, etc. On the other hand, certain styles, e.g., electric funk or anything requiring a lot of slap, sound better on a fretted bass a lot of the time. Different tools for different needs. Some people really like the sound of a fretless bass played with a plectrum.

On the other hand, I find that in a rock band I most often reach for a fretted bass.

Yup.
Totally possible to play power chords on a fretless, but not easy.
A root-five chord on a fretted bass is way easier to hit consistently, and sounds great on rock/prog/metal/punk tracks.
 
They’re their own instruments- your approach to them has to be entirely different than a fretted bass. I also think too many players toy with them, when to get really good on them, it takes commitment. In the studio, everyone wants my fretless- I can’t blame them. But they demand accuracy and a dynamic touch- nothing will amplify your deficiencies on a FL quite like the studio. Also, the detail to set up is higher too.
 
Because it’s easier. Yes, easier… once you get over the fear and learn to trust. We are much more capable than we realise. No one ever says to a violinist “wow, how do you do that without frets?” It’s just assumed that they’ve used their ears to train their fingers. It’s no big deal. Just forget everything people have ever said about fretless and back yourself. We’re amazing creatures.