He bought a house and brought his mother, his sister Beverly and her daughter, Kathy, to live with him. His father, Cleo had died of a heartache at age 48 in 1959.

The Nashville Nevada band
Bobby Austin-bass,
Roy Nichols-guitar,
WYNN STEWART-lead vocals,
George French-piano,
Peeches Price-drums,
Ralph Mooney-steel,
Carl Mortensen-club owner

Jackie Burns was a female singer who also sang with the band. While in Vegas, Wynn also landed a TV show and worked as a DJ.

Wynn (on guitar), Jackie Burns (at the microphone), Ralph Mooney (on steel)

In 1962, Bobby Austin left the band to pursue a solo career, leaving Wynn without a bass player. Merle Haggard sat in with the band while Wynn was out of town. Wynn came back unexpectedly and was standing in the crowd when he heard Merle sing some songs. He liked him and hired him to be his permanent bass player. Merle was working on a singing career himself. He really liked one of Wynn's self-penned songs, "Sing a Sad Song". Being the generous guy that he was, Wynn gave it to him and it became Merle's first hit, peaking at #19 on the country charts. Merle played with Wynn for about a year.

Wynn's first marriage was to Claire Anne Douthit on 6/24/62. They had a little boy, Greg, born on 4/23/63.

By the early 60's, Wynn's reputation was considerable and he had a string of moderate hit singles. Wynn continued to record for Challenge until 1963. "Big Big Love" was released on 12/25/61, spending 7 weeks on the charts and peaking at #18. "Another Day, Another Dollar" was released on 11/24/62 and spent 3 weeks on the charts, peaking at #27.

In 1963, Wynn and Claire were divorced. Then he met and married his 2nd wife, Dolores, while singing at the Nashville Nevada Club. They had a daughter, Wren Dee, born in March, 1964.

(the following story is in the words of Wynn's ex-wife, Dolores)

"My best friend at the time was Simone Cerrone, a high school girlfriend of mine from Cheektowoga, NY, who worked in Las Vegas as a beautician. She did Wayne Newton's mom's hair as well as Ann Margaret's. Simone and Wayne were good buddies. Jerry Newton (Wayne's brother) had a lounge act at the Freemont Hotel in 1963. I dated him occasionally. The four of us all ran around together.

"Simone and I loved to dance and the Nashville Nevada had the largest dance floor in town, not to mention great music to dance to. We went there to dance a lot. As I was dancing, I noticed this cute little guy singing on stage and I caught him watching me... several times. During the band's break, he came over and invited himself to sit at our table and offered to buy us a drink. I remember smiling as he introduced himself (as if we didn't know who he was). After several more meetings at the club, he finally asked me out and gave me a ride home. I had an apartment in Vegas and had 2 little boys (Ricky and Geno) from a previous marriage.

"While we were dating, Wynn was a disc jockey at a local radio station. He would often play songs just for me and dedicate them to me (in special code that only he and I would understand). We also often double-dated with Bobby Bare and his wife, Jeannie.

"We decided to get married, but Wynn's schedule was so busy, we ended up getting married - in between sets with the band- on the Vegas strip in a little chapel.

"Wynn was a bit of a 'momma's boy' and he was afraid to tell his mom about our marriage. He lived with his mom and his sister, Beverly. His mom was very protective of him. So even though we were married, I had to go back to my apartment, alone. After a few months, he finally got up the nerve to tell his mom that he had married again and he told her, 'by the way, there is a baby coming soon, as well'.