When it makes sense is a matter of debate. Far Eastern countries, such as S Korea and Japan, had substantial percentages of their populace masking pre-Covid. And they have had substantially lower levels of infection--not solely because of masking, of course.
Masking is a mitigation method, most useful when in enclosed spaces among crowds. As with everything in life, there are tradeoffs. But the presence of such a highly infectious agent should make everyone consider not just their own health and safety, but also that of those around them.
As to JB--he has appeared to be quite uncomfortable with wearing a mask from the very beginning. Jimmy Durante Syndrome, I would guess.