1) This could be one of the coolest Cool Picks ever posted because of the entertainer involved— Tony Bennett. Why? Because Bennett is not only a highly talented singer and a contemporary of the late Frank Sinatra, he’s also extremely friendly and polite, and always willing to work with any talented musicians. He’s won an amazing 17 Grammy Awards and recorded two duet albums with many top musicians, including Paul McCartney, Barbra Streisand, Bono, Elton John, Aretha Franklin, Lady Gaga, and Amy Winehouse. He excels at singing different musical styles, from jazz to tunes from Great American Songbo0k to standards he’s created, like “I Left My Heart in San Francisco” and “Steppin’ Out With My Baby.”
Comedian Bob Hope liked Anthony Benedetto’s singing when he first heard Bennett perform in 1949, but not the stage name, Joe Bari, that Bennett was using. Hope asked the singer what his real name was, then renamed him Tony Bennett. The octogenarian has remained a “happening” performer for six decades, and he’s an accomplished painter, too. This is a great opportunity to see a musical legend in the splendor of Heinz Hall. 8 p.m. 600 Penn Ave., Cultural District.
2) John Prine learned to play the guitar at age 14 while growing up in Maywood, Ill., and he’s been putting that talent to good use through the years. A “songwriter’s songwriter,” Prine is known for lyrics that reflect the many aspects of our human condition, including our struggle to make a living. He’s sharing that talent tonight at the Benedum Center. 8 p.m. 237 7th St., Cultural District.
3) Donna the Buffalo, a band that plays across the musical genres of folk, rock, country, bluegrass, and zydeco, hails from the Finger Lakes region of New York. Followers of the band are known collectively as “The Herd.” Opening act is Driftwood. 8 p.m. The Rex Theater, 1602 E. Carson St., South Side.
4) Actor and comedian Steve Rannazzisi has had parts in TV shows, including “The League,” “Punk’d,” and “Third Watch.” He played Stuart in the Kevin James comedy film Paul Blart: Mall Cop and performed on Comedy Central’s “Premium Blend.” He’s at Pittsburgh Improv tonight. 8 and 10:15 p.m. Runs through Sunday. 166 E. Bridge St., The Waterfront, Homestead.
5) Dancing Queen will put people on the dance floor at Jergel’s Rhythm Grille. The disco/funk band takes the stage at 9 p.m. 285 Northgate Dr., Warrendale.
6) Good Fridays at the Warhol is a weekly party at the museum, featuring art exhibits, music, and cocktails in the high temple to Andy Warhol’s numerous talents. Half-price museum admission. 5 – 10 p.m. 117 Sandusky St., North Shore.