Pizzarelli's updated old-school sound caught the ear of many jazz purists early on; notably, in 1993 the John Pizzarelli Trio opened various dates on Frank Sinatra's tour, eventually participating in the legendary vocalist's 80th birthday celebration at Carnegie Hall. Interestingly, Pizzarelli's growing popularity garnered him a lead spot in the 1997 Broadway production of Dream, a tribute to composer Johnny Mercer. His 1998 RCA release, Meets the Beatles, found him reinterpreting classic songs by the iconic Liverpool quartet, while the following year he paid tribute to one of his biggest influences, pianist/vocalist Nat King Cole, on P.S. Mr. Cole. Pizzarelli then signed with the Telarc label in 1999 and released two standards-based albums, Kisses in the Rain and Let There Be Love, in 2000.
Since then, he has recorded an album with pianist George Shearing and celebrated ten years of performing with his trio by releasing the concert album Live at Birdland in 2003. Taking a break from swing, Pizzarelli released Bossa Nova in 2004. Largely featuring the works of Brazilian composer Antonio Carlos Jobim, the album showcased the Pizzarelli Trio on such classics of the genre as "The Girl from Ipanema" and "Aguas de Marco (Waters of March)." In 2005 Pizzarelli returned to his usual fare of American standards with Knowing You (though he penned the title track), and backed by the Clayton-Hamilton Jazz Orchestra, paid his tribute to the legend himself with 2006's Dear Mr. Sinatra. ~ Matt Collar, All Music Guide