Legendary singer Tony Bennett intently taps on his iPad while sharing a story about his old friend Frank Sinatra. It's a big day for the 87-year-old musician: more than 75 of his albums are finally landing in the iTunes Music Store and he's about to set out on a full day of social networking to get the news out to a much younger audience.
"It's amazing how technology has changed the way we live and it's remarkable to think about what's ahead," Bennett told Mashable, before participating in a Twitter chat. "No one wants an autograph anymore — they just whip out their camera phones and post it to Facebook right away. Everything is so fast."
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For an artist who has been a success for more than six decades and racked up more than 17 Grammy awards along the way, he's still learning how to evolve with the industry.
As a part of an effort encouraged by his son, Bennett — clad in a suit, as always — was seemingly everywhere on the Internet on Tuesday. One hour, he was fielding questions on Twitter (via the hashtag #AskTony) and the next, he was rattling off answers on Reddit, a Q&A session that landed him on the front page of the wildly popular message board website. And then, to wrap up the day, he looked through old pictures from the Sony Records archives for a video posted in segments to his Facebook page.
Going through the archives with Sony's Tom Tierney. Tune in now at http://t.co/fylxUYzjyk. #tonydigitalday pic.twitter.com/5tUUnzC2lF
— Tony Bennett (@itstonybennett) October 8, 2013
For a man who says he barely checks his own iPhone, he owned the Internet, discussing everything from his love of painting to his upcoming jazz album with Lady Gaga due out Jan. 1.
Many who asked questions on Reddit cited their parents and grandparents as huge fans, but his recent work with younger acts such as Gaga, Carrie Underwood and the late Amy Winehouse ushered in a new wave of followers.
"My favorite story about [Winehouse] is that while everybody was mourning her death, I ran into her mother, who was a very small sweet little woman,'" he wrote on Reddit. "She said, 'I'm a little different than everybody about my daughter's death because she always had a dream of becoming famous. So even though she had a short life, she was always content because she acquired her goal.'"
Bennett's other social initiatives were a little less candid than the Reddit AMA, as followers submitted questions via Facebook and Twitter using hashtag #AskTony and #TonyDigitalDay ahead of time. Answers were prepped and posted with the help of Twitter app Long-Tweets, which lets you post tweets longer than 140 characters.
"@iTunesMusic: "Who was your most memorable collaboration?" — @TheIllestShogun #AskTony" #TonyDigitalDay pic.twitter.com/NWAiUefQrQ
— Tony Bennett (@itstonybennett) October 8, 2013
He wasn't a complete stranger to the digital world before Tuesday; he says he is loyal to his iPad while on the road: "I use a lot of art apps," Bennett, who's biggest passion aside from music is art, told Mashable. "I watch instructional videos about it too."

Among his favorite art apps are Art Authority and those by artist friends, including Charles Reid, Robert Wade and Everett Raymond Kinstler. He used to sketch on napkins and tablecloths at restaurants — so waiters and waitresses were treated to more than just a tip — but now he relies mostly on his tablet while traveling.
How else are you seeing legends adapt to the technological age? Let us know in the comments.
Images: Mashable, Christina Ascani