Natalie Cole?

Great guess! I never would have thought of her.

Is that her? If so, it is my most 'brilliant' (lucky!) guess on any level since a long, long time, haha.

I just thought, father was likely a musician during 50's-60's. Child exposed to jazz, soul and blues (though NKC was a balladeer, iirc). Father died...mother troubles likely ensued after that. Nat died in '65 which would have made Natalie 15, a 'great' age for parent/kid troubles. All of my thinking stemmed from Nat, because I know ZERO about Natalie, haha (except that she earned an exceptional career).

I'll wait for confirmation before counting my chickens

Amazing guess, Chessman! It is indeed Natalie Cole.

I recorded some demo tapes, which led to a contract with Capitol Records, and resulted in the release of my debut album.

My 1976 Grammy for Best Vocal Performance started a rivalry with Aretha Franklin, who had won eight times before losing to me.

After releasing several more successful albums, I was awarded a star on the Hollywood Walk of Fame in 1979.

In 1981, my personal problems -- including battles with drug addiction -- began to attract public notice, and my career suffered as a result.

In 1983, I entered a rehab facility in Connecticut and stayed there for a period of six months.

After switching record labels a few times, in 1987 I finally had another hit album, which included a cover of a Bruce Springsteen composition.

In 2000, I released an autobiography which described my substance abuse, including how at one stage as an addict, I worked as a prostitute's tout in order to fund my drug habit.

I announced in 2008 that I had been diagnosed with hepatitis C, which I attributed to my past intravenous drug use.

I died of congestive heart failure on the last day of December, 2015.

My most successful (and probably best-known) album sold more than 7 million copies in the U.S. alone and won several Grammys, including Album of the Year, Record of the Year and Best Traditional Pop Vocal Performance for the top song.

It featured me singing songs my famous father had recorded, nearly 20 years after I initially refused to cover my dad's songs during live concerts.

The album’s hit single was an interactive duet between myself and my late father on the title song, "Unforgettable".

Your turn …

I was born in Italy in the 2nd half of the 19th century. My family was poor, but we were never destitute. I was the 3rd of 7 children, and one of 3 of those 7 who survived infancy. I was famous enough to have a biography written about me - by my American wife!

My father was a mechanic and foundry worker who thought I should adopt the same trade, and at the age of 11 I was apprenticed to a mechanical engineer who constructed public water fountains (whenever visiting Naples in future years, I liked to point out a fountain that I helped install.) At my mother's insistence, I also attended school for a time, receiving a basic education under the tutelage of a local priest in who's church choir I sang, and my voice showed enough promise to contemplate a possible career in music.

I was encouraged in my early musical ambitions by my mother. To raise cash for my family, I found work as a street singer and performed at Cafés and soirées. I used the fees earned singing at a resort to buy my first pair of new shoes.

At the age of 22 I made my professional stage debut.

Enrico Caruso?

That's a roger, Arthur. Enrico Caruso, it is!

Wowzer!

I didn’t know much about Caruso”s life, but your references to Italy, music & singing, plus a stage debut made me think it must be an opera singer. And Caruso instantly popped into my head when I thought about someone being born in the latter half of the 1800’s.

I’ve got another one handy … started pre-preparing clues in case we get any more “drive-by-and-disappear” participants. Will post in just a little while.

I was born in Pennsylvania in 1908. Raised a Presbyterian, I was a devout church-goer for much of my life.

My father ran our family’s store, which he hoped I would take over after attending college.

My mother was a pianist, and music was an important part of family life.

Once, when a customer at the store was unable to pay his bill, my dad accepted an old accordion as payment, which I learned to play with the help of a local barber.

Lawrence Welk

Not Mr. Welk.

A shy child, I spent much of my time after school working on model airplanes, mechanical drawings, and chemistry—all with a dream of going into aviation.

Howard Hughes

(On second thought, scratch that; not a church-goer.)

Due to scarlet fever that turned into a kidney infection, I had to take time out from school in 1927, which delayed my graduation for a year.

I remained passionate about aviation, with my interest enhanced by Charles Lindbergh's first solo transatlantic flight.

Charles Lindbergh?

And, great job on naming Caruso!

You ought to know I’m a music aficionado, Chessmann! Besides, I was raised in a house full of classical music, which led to years of musical studies and a music career.

Back to the clues:

I enrolled at Princeton in 1928, majoring in architecture and becoming a member of the Princeton Charter Club.

After the United States entered the Second World War in 1941, I enlisted as a private in the Army Air Corps.

Amelia Earhart

Not the great Amelia.

After fighting in the European theater, I attained the rank of colonel and received several awards for my service.

Chuck Yeager