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Dean Martin, the "King of Cool," never recovered after he lost his "golden boy."

The ‘50s crooner and member of the Rat Pack was struck by tragedy in 1985 following a lustrous Hollywood career. A military jet carrying his oldest son, Dean Paul Martin, crashed into the side of a mountain during a routine exercise in 1987. Martin's son was 35 at the time of his death.

"Dean Martin’s final years were very, very sad after he lost his son," author William Keck told Fox News Digital. "It was like looking at a candle without a flame."

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A close-up of Dean Martin wearing a gray suit and a black tie.

Dean Martin never recovered from his son's tragic death, said author William Keck. (Henry Gris/FPG/Getty Images)

Keck, a former reporter for the National Enquirer, has written a new memoir about his decades-long career, "When You Step Upon a Star: Cringeworthy Confessions of a Tabloid Bad Boy." In it, he details the celebrities he befriended, protected and wronged.

Keck, who reported on Martin’s final years, said the singer was someone he was eager to protect.

"He was still the nice man that he seemed to be on television," said Keck. "He would always greet me when I came over to his table. He would always say, ‘I’ll be back on that stage one day. You’ll see me.’ But he was done."

Dean Martin stepping out of a car in a blue leather jacket and brown pants

Dean Martin is seen here in August 1995. He died on Christmas Day that year. (Getty Images)

"He would eat by himself, always wearing the same outfit," Keck recalled "It was navy pants and a light blue shirt. He would order the same dish — clams casino. He would just let the clam juice drip down his shirt. At a nearby table would be his ex-wife Jeanne… It was very strange to observe. It was like seeing a wax figure that was barely moving around."

Book cover for When You Step Upon a Star.

William Keck's book, "When You Step Upon a Star," is available in bookstores now. (Jacobs Brown Media Group )

In his book, Keck described how Martin was suffering from "a broken heart" after losing his son. He claimed that every evening, Martin would go to the same Italian restaurant in Beverly Hills, La Famiglia, where the same dish awaited him. He was always spotted quietly twirling his pasta as he sat alone.

Martin would always smile at Keck whenever he spotted the young writer. Martin even allowed Keck to take photos of him for his stories.

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A close-up of Dean Martin wearing his blue jacket and glasses.

Dean Martin is seen arriving at his favorite restaurant, La Famiglia, in 1994. (David Keeler/Getty Images)

"The problem was that it always looked like the same photo because he would wear the same outfit every time," Keck explained. "You weren’t sure if it was taken six months ago or a year ago."

Keck said he spoke to numerous pals to gain insight into what Martin’s life was like outside the spotlight. It was clear the patriarch was hurting.

Dean Paul, nicknamed "Dino Jr.," was a jack of all trades. According to People magazine, he made his mark with tennis and had a rock band with pals Desi Arnaz Jr. and Billy Hinsche. He eventually followed in his father’s footsteps and pursued acting. That led to a Golden Globe nomination for his role in the 1979 film "Players."

Dean Paul Martin holding a tennis racket.

Dean Paul Martin Jr., circa 1977. (Reed Saxon/IMAGES/Getty Images)

According to the outlet, Dean Paul was also a semi-professional football player, race car driver and pre-med student. But it appeared he finally found his calling when he became a pilot with the Air National Guard in 1981.

"I’m proud of him," Martin was quoted as saying by the outlet. "I’d be proud even if he didn’t become a jet pilot because he’s a good boy. He just doesn’t know what he wants to be."

According to The New York Times, Dean Paul and Capt. Ramon Ortiz, 39, were in one of three F4-C Phantom jets that were flying maneuvers near the San Bernadino Mountain range. The plane was lost and the remains of both men were found six days later.

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Dean Paul Martin wearing a light blue shirt and a grey suit.

Dean Paul Martin died in 1987 at the age of 35. (Ron Galella/Ron Galella Collection via Getty Images)

''Capt. Dean Paul Martin and Capt. Ramon Ortiz perished instantly at the time of impact,'' Sgt. Carolyn Hamilton, an Air National Guard spokeswoman, said at the time.

According to officials, the jet piloted by Dean Paul plunged nearly 4,000 feet from its last radar altitude reading of 9,300 feet. The outlet noted that it hit the side of the mountain at about 400 miles an hour.

"[Dean Paul's] death had a huge impact on Dean Martin," said Keck. "Everyone who knew Dean Martin would tell you that. And it was [his pal] Rich Little who told me that once he lost his son, that was the end of him. That was a big part of him that died and never recovered."

Dean Martin surrounded by his children as he holds a guitar.

Dean Martin is seen with his children and wife Jeanne in Los Angeles. (Martin Mills/Getty Images)

The Associated Press quoted singer Paul Anka as saying that the death of Martin’s son was "a huge turning point."

"After that event in his life, things really changed," said Anka.

Martin passed away at his Beverly Hills home on Christmas Day 1995. He was 78.

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Dean Martin smiling next to Frank Sinatra as they both wear tuxes.

Dean Martin is seen here in 1979, during happier times, with his pal Frank Sinatra. (Bob V. Noble/Fotos International/Getty Images)

"In a way, he fooled us," said Keck. "He kept going. I remember we weren’t going to miss his funeral. It was a private VIP service with all of these celebrities. Everyone wanted to pay their respects. I remember at one point it just got dark. All you could hear was Rosemary Clooney, George Clooney’s aunt, singing ‘Everybody Loves Somebody.'"

"It was completely surreal," Keck admitted. "In the end, it was a friend paying tribute to him."

Keck said his memories of greeting Martin at the same restaurant for his stories are bittersweet.

Dean Martin smiling in a blue jacket and a white shirt.

William Keck said his memories of Dean Martin are bittersweet. (Ron Galella, Ltd./Ron Galella Collection via Getty Images)

"I remember him always greeting me with that warm smile," said Keck. "It was heartbreaking. I don’t think his broken heart ever healed."

The Associated Press contributed to this report.