Jonathan Winters?

9. The Chicago Tribune called me “a charismatic performer who speaks with the resonant tones of a Shakespearean.”

Jay Thomas

10. Although I legally changed my name to a nom de plume, I still use my birth name for technical writings.

Mr.Goldstein.

As per usual, you got it, Landmark! The answer was Max Maven (born Philip Goldstein).

11. Reviewers have praised my work, describing my performances as “impossible”, “inexplicable”, ”spellbinding”, and “mesmerizing”.

12. I am ranked as one of the 100 "Most Influential Magicians of the 20th Century" by Magic Magazine.

13. The New York Daily News called me ”the country's premier mindreader."

You’re up …

The Shakespearean voice and the nom de plume clues led me to remember that Max started in Boston.

1. I was a Pulitzer Prize winning author, though that's not my main claim to fame (Heck, I probably didn't even write most of the book)

2. When I was about 10, my family relocated to NYC by taking our private railway car there.

3. The summer before college I worked as a ranch hand on a 40,000 acre cattle ranch.

4. Despite high school and college years plagued with various illnesses, I was on the varsity swim team in college.
5. That was one skill that came in very handy later on in the Navy.
6. I participated in a television first.

JFK?

Correct! That debate in 1960 was the first televised one; and when PT-109 got hit, JFK swam miles. Ted Sorenson admitted to writing most of Profiles in Courage.

Yes, some bits I was familiar with here and there just all came together for me. I didn't know "Profiles" won a Pulitzer, but the Navy and the television first - which for some reason that debate instantly came to mind - seemed to find their own way of directing me, haha.

I'm going to have to pass to another participant for the next one.

If you never heard of my mystery guest, you must be living in a cave. This one is not obscure. This one is a household name. I promise.

1. I was born in 1969 and raised in the Los Angeles Area of California
2. My parents were engineers working on space technology
3. You don't know me by my first name, I use a nickname that comes from my middle name.

4. My father converted to Judaism to be with my mother.

5. School was hard for me. I attended schools that offered assistance for students having trouble with regular schooling.

6. By tenth grade I was already strongly involved with cocaine.

7. I soon dropped out of high school, and started a band. I am a singer, songwriter and guitar player... Yet that is not what I am best known for.

8. THough being a drop out, I managed to get into UCLA (hard to do) where I caught a break and met Tim Robbins.

Jack Black?

I believe 'TH' (#8) is the BIG clue?

No, it is a typo.