Inside Roger Moore's Private World, His Heartbreak Over Daughter's Death — and His Colorful Love Life

Roger Moore's life off-screen was as colorful as his danger-filled adventures as James Bond.

The legendary actor died at the age of 89 after decades of memorable roles on-screen — but his private life was just as full. The actor had his share of torrid romances in his younger days before finding happiness with his fourth wife, Kiki Tholstrup, and settling into a life of charity and luxury in Switzerland.

Though the actor enjoyed decades of success thanks to his early television work and, eventually, his celebrated turn as 007, his later years were quieter as he dedicated himself to charity. Here's a look back at the private world of a debonair star — one filled with both triumph and tragedy.

A Father's Heartbreak

In the summer of 2016, tragedy struck Moore and Tholstrup when Christina Knudsen — Tholstrup's daughter from a previous relationship — lost her battle with cancer at the age of 47. The actor paid tribute to Knudsen, who was lovingly called Flossie, in several tweets after her death, both accompanied by a picture of the late Scandinavian blonde.

Knudsen and Moore in 2010

"Our beautiful daughter Christina (a.k.a. Flossie) lost her battle with cancer 25 July at 10am. We are heartbroken," Moore wrote, later adding, "We were all with her, surrounding her with love, at the end."'

Knudsen credited Moore with being a key and positive male influence in her life after her father and stepfather had died.

Ups and Downs in Love

The actor was married four times, the first three ending in turmoil before he finally married Tholstrup. "I've been married four times and caused a great deal of hurt and upset around me," Moore told The Guardian in 2012. "I'm a selfish bastard, but I'm just very, very happy that Kristina and I found one another."

Moore and Tholstrup

His first marriage came when he was just 18 — to actress and ice skater Doorn van Steyn in 1946. The couple split in 1953 after Moore met his soon-to-be second wife, Dorothy Squires.

Squires was 13 years older than Moore, and they married in 1952, soon after the actor divorced his first wife. Theirs would be a tumultuous relationship. The marriage eventually crumbled following several miscarriages, and Moore left Squires in 1961 for Italian actress Luisa Mattioli, whom he met in 1962's The Rape of the Sabine Women.

Squires, however, would not accept the breakup, and she sued Moore multiple times for ending their relationship. She finally granted Moore a divorce in 1969, and he wed Mattioli soon after. (Squires would eventually be diagnosed with cancer, and Moore later paid for her treatment and hospital bills. She died in 1998.)

Moore and a one-year-old Christian on the set of The Man with the Golden Gun

Moore and his third wife, Mattioli, had three children — Deborah, Geoffrey and Christian — and stayed together until 1993, the same year when Moore was diagnosed with prostate cancer. The diagnosis, he told Evening Standard in 2012, prompted him to reevaluate his life — and realize he had fallen out of love with Mattioli.

It was actually through Mattioli that Moore met Tholstrup — the two women were friends — and he started dating the Swedish socialite in 1993. Mattioli, however, was enraged by their romance and refused to grant the actor a divorce until 2000. Moore and Tholstrup finally wed in 2002. Mattioli passed away in 2021.

Charity Work

Moore took a step back from acting later in life and dedicated himself to charity, working closely with UNICEF. Inspired by his good friend Audrey Hepburn's commitment to the U.N. charity, Moore was named a UNICEF Goodwill Ambassador in 1991 and continued working closely with the organization as a special ambassador until his death.

"Most of my time these days is spent with UNICEF, raising awareness and raising funds," Moore told Entertainment Weekly in 2012 when asked about upcoming projects.

Moore in Guatemala with UNICEF in 1991

In 2003, the actor was honored with the Humanitarian of the Year Award for his services to UNICEF. Queen Elizabeth II later named him a Commander of the Order of the British Empire (CBE) in 1999 and a Knight Commander of the Order of the British Empire (KBE) in 2003 for his acting and charity work.

UNICEF USA president and CEO Caryl M. Stern paid tribute to the late actor in a statement to PEOPLE.

"Sir Roger Moore will be remembered not only for his role as the iconic secret agent James Bond but by his UNICEF family for his longstanding service as a Goodwill Ambassador," she said. "His storied career was matched off-screen by his commitment to put children first and the many lives he touched through this work. Today we mourn the loss of a dear friend, a great humanitarian and a true champion for the world's children."

Moore also worked closely with the Angiogenesis Foundation on global health and disease prevention programs. "Beyond his international fame in film, Sir Roger's charitable work will be an enduring legacy," Dr. William W. Li, President of the Angiogenesis Foundation, said in a statement to PEOPLE. "He impacted countless lives and was a man of incredible character, integrity, and dignity. We are honored to have had his guidance and support of our Foundation's work."