For the record, annotations are fine. I basically just wanted the first three that popped into your mind upon hearing the question.
And I outsmarted myself - With more than a moment’s thought I would have selected Johnny Carson in place of David Letterman.
mmm
The leader board so far:
Bob Dylan – 7
J.R.R. Tolkein - 4
Stan Lee – 3
David Bowie -2
Stephen King – 2
Elmore Leonard – 2
David Letterman – 2
George Lucas – 2
Dolly Parton – 2
Terry Pratchett – 2
Ayn Rand – 2
Pete Seeger – 2
Quintin Tarantino – 2
Frank Zappa – 2
I was disappointed with myself that the first three I came up with were all male. But as you form these connections at a certain time in your life, you can only work with what you’re given. Though I admire loads of women across pop culture, I can’t really say they are heroes or inspirations in the way you’re looking for. I think maybe if I had instead been born 20 years ago, choosing my heroes from today, I’d find a lot more women to choose from.
While I appreciate your perspective, even with the luxury of time there would not be a woman in my top 3.
There is nothing to read into that statement other than Dylan, Carlin, and Carson are at the top of my personal heap.
(and a quick calculation of the results so far indicate that females make up just 15% of the responses)
mmm
Kurt Vonnegut
Bill Hicks
Keith Jarrett
That’s a good’un.
Billie Holiday
Hoagy Carmichael
Mark E. Smith
I might chosen Billie Holiday if I had thought for a little longer.
Barack Obama
Cooking program contestants who draw the line and obey it*
Paul McCartney
Oprah
*E.g. on the Food Truck Race there was a vegan truck who chose not to participate in a challenge that required the use of meat. And there was a Waffle Truck whose staff took an hour to go to church while others sold. And on there was a Jewish chef on Chopped who cooked what was given but wouldn’t taste her dish because it had pork in it.
We watch a lot of cooking related programs but really, any contestant who risks losing by following their own rules is ok by me.
I notice OP is tallying, so I gave a fourth to make that easier. Name another black woman that had the impact Oprah has had?
Kurt Cobain
Terry Pratchett
Tarantino
Madonna
Quentin Tarantino
Sir Patrick Stewart
Thanks. But y’know, I’m amazed that I’m the only person to list Muhammad Ali. Is there something negative about his legacy in the US that I just don’t see in the UK?
j
There are a lot of sports figures and only 3 choices. 3 quick choices at that. For me, I’m baseball oriented so Lou Gehrig and Jackie Robinson are the first two I thought of. Ali would come up much later. But he is a good choice, a much larger than life figure.
And as importantly, a figure who was bigger and more important beyond his sport than within it, I would argue. I guess that’s why I’m so puzzled at the lack of love.
As an aside, in his heyday, UK sports commentator Harry Carpenter proposed that if you were parachuted anywhere in the world, a place unknown to you where you did not speak the language, the two words that could be guaranteed to elicit a smile from the first person you met would be “Muhammad Ali”.
j
Not in my book. He would definitely make my Top 10.
Without having read others posts;
R.G. LeTourneau
Jim Kelly of JPL fame.
John Muir of “The Idiot Book” fame.
These are listed in no particular order except that this is the order they came to mind. Actually my 4th came to mind first, but no one has heard of him.
If allowed a 4th, 5th & 6th,
My uncle Tabor, who helped raise me.
Amelia Earhart. Who lived her life as she saw fit.
My aunt Martha, Ditto above.
I suspect you have not respected the terms of the OP. I will let it pass, but will he? 
Tony Iommi - Black Sabbath guitarist
Meaghan Benfeito - Canadian Olympic diver
I can’t give a third without breaking the no more than three rule 
UPDATE:
Bob Dylan – 7
Quentin Tarantino – 4
J.R.R. Tolkein – 4
Stan Lee – 3
Terry Pratchett – 3
David Bowie -2
Stephen King – 2
Elmore Leonard – 2
David Letterman – 2
George Lucas – 2
Paul McCartney – 2
Dolly Parton – 2
Ayn Rand – 2
Pete Seeger – 2
Patrick Stewart – 2
Frank Zappa – 2
That was in fact my point. I was disappointed in myself for not having a woman in my list, and then I thought about it and couldn’t think of one at all, and was disappointed in myself even further.
The “your” in my post was a general “you” and not actually you.
I didn’t notice until after I posted, but I had two blacks, a woman and a gay – four out of three. Who’da thunk it, from a guy who is constantly modded for misogynistic and racist hate speech?