Man, this is a very tough question to answer.
So, I’ll answer by decades
1950’s - Elvis's biggest regret is that he did not demand that his beloved mother get immediate and consistent medical and mental health care, Gladys Love (Smith) Presley, died on August 14, 1958, at the age of 42 (Elvis thought but she was really 46 she changed her date of birth on her marriage certificate) and Elvis knew she was unwell and had been drinking heavily and complaining of health issues. Elvis admitted that his broken heart, of being away from her, clouded his judgment about getting her seen by great doctors and hospitals.
What I would have changed is to require Gladys to be seen by the best specialists/doctors/hospitals in the United States and assured her 24/7 that she would be in housing wherever I was stationed and that she would always be priority # 1
1960’s - Elvis regretted many of his movies during this decade. Elvis NEVER got a script to read and approve of OR decline. Elvis was locked into doing 3 movies a year and was booked, on average, 4 years in advance. During this time Elvis was the highest-paid movie star, as he got a million dollars a picture and a % of the revenue. Elvis is the ONLY actor whose movies always made money and Hollywood is notorious for its “accounting” whereby the biggest blockbuster movies, making billions, somehow end up as a loss. Elvis was ashamed of the duplicate plots. He was ashamed of the way he looked in many of the movies. He hated the songs. He complained for years and it got so bad Elvis got physically sick. He was literally….trapped.
What I would have changed is to demand, and get prior script approval AND receive any/every available song (i.e. Colonel Parker ended up structuring a music publishing company and they demanded 50% of the proceeds from the songwriters meaning the Colonel and Elvis, if he recorded their song, got 50% as if they were co-writers) and have final song(s) approval. I would have done a max of 2 movies per year and required a larger per-motion-picture fee from $ 1 million per picture to $ 1.5 million per picture.
1970’s - Elvis regretted never leaving the United States to do live concerts even though he was offered millions per concert. Colonel Parker got Elvis to believe that security would be a problem. That Elvis carrying guns would be a problem and most of all Elvis's dependency on prescription drugs would be monitored Elvis may have been subject to legal issues (i.e. due to the number of medications per fill meaning Elvis filled hundreds of medications per fill so if he had 3 prescriptions he could end up with 600 pills. Dr Nick explained during the trial whereby his physician license was in question as he was being investigated after Elvis (sadly) died on August 16, 1977. The real reason was that Colonel Parker was an illegal alien and traveling to other countries may have exposed this and Colonel could not have allowed that.
What I would have changed is that I would go overseas and do concerts. They would all be top-notch productions and they would have sold out. Also, it would have been a goal that Elvis would have worked his weight off. Perhaps he would have cut back on the medications. Perhaps, he would have gotten healthier. The pent-up demand would have kept Elvis busy for decades. One caveat is that Elvis should have plenty of time to recover and to see the countries he was appearing at which he would have enjoyed.
Take care
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