Brutally hard category, but here goes...
First, I'm nowhere near familiar enough with opera or classical to even really know where to start there. I like opera, jazz, classical, etc., but outside of a few megahuge names (Pavarotti) I just don't know. So, most of my initial, "Oh, that guy!" thoughts come from pop/rock.
Second, it's really hard to parse this with male vs. female vocalists. There are a lot of greats in each sex and I want to cheat and have two lists. But that's not the challenge, so... I'll try to be good. Gonna include an honourable mention category, though...
Third, my final choices aren't just based on octave range or ability. They're based on who brings some feeling in. Who has the vibes - that's important. Ability is good, but passion is great. Not that I'm picking a passionate tone-deaf warbler.
The List:
1. Ella Fitzgerald - I do know *some* jazz people and Ella hits that top. She's got the style, the spirit, and the pipes.
2. David Bowie - because you can feel the story with this guy. Whether he's cheekily singing about introducing you to the gang, eerily telling you about the man who sold the world, or droning in a preternatural, godlike way about the blackstar, Bowie knew the notes and the assignment.
3. I don't know his name. Seriously, I don't know the name of my third choice. There is this recording of a homeless guy singing, "Jesus' Blood Never Failed Me Yet." It was put into a loop by Gavin Bryars, orchestration put behind it, and listening to this guy with nothing singing about transcendent love makes me tear up in ways that polished, famous rock stars and opera singers just can't. If he had a second song that I'd heard, I'd probably bump him up, too.
Honourable Mentions: Louis Armstrong, Melinda (from youtube!), Bob Dylan (I know; don't care, he sings from the gut), Tom Waits, Debbie Harry, the Larkin Poe sisters, Etta James, Mick Jagger, 3/4 Beatles (...sorry Ringo...), Steve Marriott, Ted Neeley, and this guy (Dimash) https://www.youtube.com/watch?v=dYmEckJj8sk
Oh, and if I answered this again in a week, I'd probably answer almost completely differently given the wealth of vocal talent out there. But this is how I feel about it tonight.
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