“…God had a plan.
And his plan for me was…
You’re going to be in show business. And you’re going to have your network television show with 36 million people watching you, so you can help people.
That is the whole reason I breathe.”

– Tony Orlando

A Life in Song and Service: An Interview with Tony Orlando

It is an honour to step into the world of a true entertainment veteran like Tony Orlando. With a career spanning 64 years, he has touched countless lives through his music and his profound dedication to service, particularly to veterans.

More than just a performer, Tony Orlando’s journey is one of unexpected turns, deep personal connections, and a commitment to using his platform for good.

Prepare to delve into the extraordinary life and career of a true show business veteran in this insightful video interview. With 64 years in the industry, Tony Orlando shares many stories and reflections that go far beyond the hits that made him famous worldwide.

Click here to watch the full video.

From Doo-Wop Dreams to Music Mogul

Young Michael Anthony Orlando Cassavetes dreamed of being a baseball player and was part of a doo-wop group called the Five Gents. Born in New York City, his background is unique: his father was Greek, and his mother was Puerto Rican, making him a “Greek-Orikan,” a rare breed.

Though he only went to the eighth grade, fate had other plans. His first hit record as a singer was “Halfway to Paradise,” written by Carole King and Gerry Goffin.

Barry Mann and Cynthia Weil wrote his second hit, “Bless You. ” These four songwriters became some of the most essential rock and roll and rhythm and blues writers of the 20th century, inspiring even the Beatles.

The landscape of American music shifted dramatically with the British Invasion, making it difficult for American acts to get airplay. Tony, needing to earn a living, especially as he was married young and had a stepson, received a call from Clive Davis.

Davis, who knew Tony when he signed with Epic Records at 16, asked him to be the General Manager of Columbia Music, CBS Music. Despite his eighth-grade education and lack of business knowledge, Davis bet on him, focusing on his intuition. Tony excelled in this role, signing Barry Manilow to Bell Records, a singles-oriented label.

The Unexpected Voice of “Dawn”

While serving as Vice President of Columbia Music, a friend named Hank Medress from The Tokens approached Tony, who was broke and needed assistance selling a song master. The song was “Candida.” Tony agreed to help by connecting Hank with Bell Records.

Bell Records’ president liked the song but wanted a different lead voice. Hank asked Tony to sing it, reminding him of his past doing demos for Carole King. Despite his reluctance and fear of losing his executive job, Tony agreed to record it in one hour, insisting his name not be used. They recorded the song line by line in 45 minutes.

Months later, “Candida” was a smash hit. The follow-up song was “Knock Three Times,” which initially didn’t impress everyone, but Tony recorded it, and it became his biggest seller, selling four million records.

The success of “Candida” and “Knock Three Times” created a dilemma for Tony, who was still an executive hiding his identity as the singer ‘Don’. Clive Davis, however, already knew, calling it the “worst-kept secret in this business”. Davis encouraged him to pursue performing, telling him he could always return.

“Tie a Yellow Ribbon”: More Than Just a Song

Despite his reservations about recording “Tie a Yellow Ribbon Around the Old Oak Tree,” as it was not his preferred R&B style, Tony agreed to the project on the condition that background singers Telma and Joyce—who had previously sung vocals on hits like “I Heard It Through the Grapevine” and “Shaft”—would receive solo spots on the album to help promote the group “Tony Orlando and Dawn.”

The song became a hit, leading to a pivotal moment. Bob Hope called Tony, having heard the music on the radio and wanting him to open a homecoming show for POWs returning from Vietnam, Cambodia, and Laos, and performing “Yellow Ribbon” for 70,000 people, including over 500 POWs, and seeing them sing along deeply impacted Tony.

One POW told him he kept time to the song with his toe in his shoe while imprisoned. This experience led Tony to dedicate the music and everything he does to veterans from that day forward. He has reunited with the POWs every year since 1973 and was made an honorary POW. “Yellow Ribbon” has become a significant tool for fundraising for the nation, troops, veterans, and their families.

A Champion for Veterans and Others

Tony’s commitment to veterans extends beyond music. He works closely with and serves on the board of Tribute to Valor, an organization founded by Medal of Honor recipient Gary Luttrell.

The organization focuses on teaching young people the six core values that Medal of Honor recipients live by, inspiring them, and showing them possibilities they never imagined, including trips to NASA. Tony sees supporting this work as investing in the future of the country. He considers himself, Lee Greenwood, and Gary Sinise as the “three musketeers” who go to battle for veterans.

His understanding of service and empathy was shaped early in life. His sister Rhonda, who had severe intellectual disabilities, was his mentor. Caring for her taught him the importance of finding and alleviating suffering, which he calls “scratching my itch”. This lesson informed his perspective on using his success to help others.

Tony also shares stories of his friendships and collaborations, including his close relationship with Jerry Lewis, with whom he worked for 33 years. He highlights Jerry’s visits to sick children and the significant impact of the telethons on advancing DNA science, which has enabled the finding and identification of fallen soldiers.

Current Endeavours and Reflections

While Tony announced his retirement from touring after 64 years, he continues to perform for veterans. He also hosts a successful radio show, “Saturday Nights with Tony Orlando,” on WABC New York, which streams internationally. This show allows him to give a platform to other artists and friends, including Adam Sandler, Lionel Richie, and Clive Davis.

Looking ahead, Tony is embracing new creative outlets. He is writing a new book to share his life’s good, bad, and ugly with his children. He is also working on a Broadway show about his life called “Rooftop Dreams,” co-written with Michael Amartian. The show will incorporate new songs alongside his hits and focus on the tradition of Broadway musicals rather than being a jukebox show.

Reflecting on his life, Tony has “not one regret” about his career or experiences. His only regret is not being a better steward of his money, spending it instead of saving for his family, a lesson he shares with those experiencing early success.

He emphasises that giving back is the most satisfying part of living. When asked for advice for young people struggling today, he suggests asking themselves “Who am I?” and focusing on the positive aspects, realising they are “okay”.

Tony Orlando’s story is a testament to resilience, talent, and the enduring power of kindness and service. His journey from a young singer to a music executive and global star, marked by deep personal connections and an unwavering commitment to veterans, illustrates a life well-lived and dedicated to making a difference.

His final performance felt like attending his eulogy, witnessing his love and impact on others, and stepping into a new phase of life as Michael, no longer defined solely by the stage name Tony Orlando.

Watch Now: See Tony Orlando Share Decades of Heartfelt Stories and Insights.

This article only scratches the surface of the incredible depth and candour shared in this interview. To truly grasp the richness of Tony Orlando’s journey, from his Greek-Orikan roots and earliest days in the industry to his profound dedication to veterans, his encounters with legends like Bob Hope and Jerry Lewis, and the fascinating, sometimes surprising, stories behind the hits and relationships that defined eras, you need to watch the full documentary.

Hear directly from Tony about the distinction between the performer and the man, his lessons on life, service, and the entertainment business, and the emotional moments that have shaped his path. This is a rare opportunity to gain intimate insight into a career spanning 64 years, filled with honesty, humour, and heartfelt reflection. Do not just read about it, experience it firsthand.

Watch the Full Video Interview