Since his comeback, Bennett has financially prospered; by 1999, his assets were worth $15 to 20 million. He had no intention of retiring, saying "If you study the masters — Picasso, Jack Benny, Fred Astaire — right up to the day they died, they were performing. If you are creative, you get busier as you get older." Indeed, Bennett has continued to record and tour steadily, doing 100 to 200 shows a year. In concert Bennett often makes a point of singing one song (usually "Fly Me to the Moon") without any microphone or amplification, demonstrating to younger audience members the lost art of vocal projection. One show,
Tony Bennett's Wonderful World: Live From San Francisco, was made into a PBS special. Bennett also created the idea behind, and starred in the first of, the A&E Network's popular
Live By Request series, for which he won an Emmy Award. In addition to numerous television guest performances, Bennett has had cameo appearances as himself in films such as
The Scout,
Analyze This, and
Bruce Almighty. Bennett also published
The Good Life: The Autobiography of Tony Bennett in 1998.
A series of albums, often based on themes (Duke Ellington, Louis Armstrong, Billie Holiday, blues, duets) has met with good acceptance; Bennett has won seven more Best Traditional Pop Vocal Performance or Best Traditional Pop Vocal Album Grammys in the subsequent years, most recently for the year 2006. Bennett has sold over 50 million records worldwide during his career.
Accolades came to Bennett. For his contribution to the recording industry, Tony Bennett was given a star on the Hollywood Walk of Fame at 1560 Vine Street. Bennett was inducted into the Big Band and Jazz Hall of Fame in 1997, was awarded the Grammy Lifetime Achievement Award in 2001, and received a lifetime achievement award from the American Society of Composers, Authors, and Publishers (ASCAP) in 2002. In 2002,
Q magazine named Tony Bennett in their list of the "50 Bands To See Before You Die". On December 4, 2005, Bennett was the recipient of a Kennedy Center Honor. Later, a theatrical musical revue of his songs, called
I Left My Heart: A Salute to the Music of Tony Bennett was created and featured some of his best-known songs such as "I Left My Heart in San Francisco", "Because of You", and "Wonderful". The following year, Bennett was inducted into the Long Island Music Hall of Fame.
Bennett frequently donates his time to charitable causes, to the extent that he is sometimes nicknamed "Tony Benefit". In April 2002, he joined Michael Jackson, Chris Tucker and former President Bill Clinton in a fundraiser for the Democratic National Committee at New York's Apollo Theater. He has also recorded public service announcements for Civitan International. In the late 1980s, Bennett entered into a long-term romantic relationship with Susan Crow (born c. 1960), a former New York City schoolteacher. Together they founded Exploring the Arts, a charitable organization dedicated to creating, promoting, and supporting arts education. At the same time they founded (and named after Bennett's friend) the Frank Sinatra School of the Arts in Queens, a public high school dedicated to teaching the performing arts, which opened in 2001 and would have a very high graduation rate. It was a tribute in return, for in a 1965
Life magazine interview Sinatra had said that:
- "For my money, Tony Bennett is the best singer in the business. He excites me when I watch him. He moves me. He's the singer who gets across what the composer has in mind, and probably a little more."
Danny Bennett continues to be Tony's manager while Dae Bennett is a recording engineer who has worked on a number of Tony's projects and who has opened Bennett Studios in Englewood, New Jersey. Tony's younger daughter Antonia is an aspiring jazz singer.
In August 2006, Bennett turned eighty years old. The birthday itself was an occasion for publicity, which then extended through the rest of the following year.
An American Classic reached the highest place ever on the albums chart for an album by Bennett and garnered two Grammy Awards; concerts were given, including a high-profile one for New York radio station WLTW-FM; a performance was done with Christina Aguilera and a comedy sketch was made with affectionate Bennett impressionist Alec Baldwin on
Saturday Night Live; a Thanksgiving-time, Rob Marshall-directed television special
Tony Bennett: An American Classic on NBC, which would win multiple Emmy Awards; receipt of the Billboard Century Award; and guest-mentoring on
American Idol season 6 as well as performing during its finale. He received the United Nations High Commissioner for Refugees' Humanitarian Award. Bennett was awarded the National Endowment for the Arts Jazz Masters Award in 2006, the highest honor that the United States bestows upon jazz musicians.
On June 21, 2007, Bennett married long-time girlfriend Susan Crow in a private civil ceremony in New York that was witnessed by former Governor Mario Cuomo.
The year 2008 saw Bennett making two appearances on "New York State of Mind" with Billy Joel at the final concerts given at Shea Stadium, and in October releasing the album
A Swingin' Christmas with The Count Basie Big Band, for which he made a number of promotional appearances at holiday time. In 2009, Bennett performed at the conclusion of the final Macworld Conference & Expo for Apple Inc., singing the "The Best Is Yet to Come" and "I Left My Heart In San Francisco" to a standing ovation, and later making his Jazz Fest debut in New Orleans. In February 2010, Bennett was one of over 70 artists singing on "25 for Haiti", a charity single in aid of the 2010 Haiti earthquake.