It is rare that an artist can cross generations and also appeal to all types of people. We are talking about a career spanning six decades and over 50 million records sold.
The Rolling Stones have been around forever, but they haven't been relevant since Microsoft used Start Me Up to roll out Windows 95 (I think Windows hasn't been relevant since '95 too).
Bob Dylan has been around for just as long, but I do not think Dylan has the pop appeal that can spawn two successful duet albums with current pop artists like Bennett will release soon. Can you imagine a Dylan-Beiber mashup... "Baby Baby Oh- Nooo."
So what is it about the beauty of Bennett where the boys still think he is cool and the girls find him is classy?
I believe there are 3 characteristics modeled in the man Tony Bennett that we can take into our own heart and soul. And they go beyond being a smooth singer and slick Italian.
There are a lot of artists who insist you know how great they are, ala Kanye West; not so with Tony Bennett. He has been a hard worker understanding the weight of his career without ever having to brag about it. You would never see Bennett take an award from a Taylor Swift bringing her to tears. You would see, however, Bennett give an award to Amy Winehouse that would bring her to tears, simply because of her respect for Tony.
It seems as if every picture of Tony Bennett comes with a smile. A certain smirk that relaxes you and also conveys the idea that he might be up to something. He never takes himself too seriously and there is something really endearing about that in an accomplished musician. You can see Bennett's slick wit in this quote addressing his popularity, "I think one of the reasons I'm popular again is because I'm wearing a tie. You have to be different."
Tony Bennett has a big smile but he has bigger heart. You can find Bennett connected to seven charities (American Cancer Society, Andre Agassi Charitable Foundation, Exploring The Arts, Griffith Park Recovery Fund, MusiCares, Neurofibromatosis, Inc., Starkey Hearing Foundation) as well as supporting eight causes (At-Risk/Disadvantaged Youths, Cancer, Children, Creative Arts, Education, Health, Miscellaneous, Unemployment/Career Support). His philanthropy is commendable but it is how he talks and sees people that really shows the compassion of Bennett. In a recent interview about his duet (Lady is a Tramp) with Lady Gaga, she said "I'm a tramp," to Tony's reply, "No No No you're a lady playing a tramp." It is that type of heart we need to have that is described in the verse Philippians 2.3 to consider others better than yourself.
Check out this interview that captures the Beauty of Bennett featuring his new duets album some great current artists and also his connection with Amy Winehouse.