Crooners—legitimate heavyweights who can elicit shrieks, tears and piles of ladies' undergarments from their audiences—are few and far between these days. 

But this week, two of the biggest come to Portland. The first of them turns 85 this August. That's not stopping the redoubtable Tony Bennett—once called "the best singer in the business"—from touring the world, belting out the classics and standards that made him famous more than half a century ago.

The other Portland-bound crooner, 32-year-old R&B sensation Usher, is his generation's closest approximation of Michael Jackson: a singer, dancer, businessman and personality of monstrous proportions with huge commercial appeal and an even greater influence on young artists. Though Usher rose to prominence at a young age, his hits are often primarily concerned with letting listeners know that the singer is a full-grown man. We thought we'd examine the generation gap between some of Bennett's and Usher's biggest hits.


"I Left My Heart in San Francisco": Bennett's signature number, this 1962 classic is a paean to a city "where little cable cars climb halfway to the stars." The narrator has been left cold by Paris, Rome and Manhattan and dreams of returning to the place his heart calls home. (RS)

"Dream a Little Dream of Me": From his 2002 album of duets with K.D. Lang, A Wonderful World, this unlikely pairing—a then-septuagenarian crooner with a far younger lesbian chanteuse—is surprisingly sultry. Bennett's wistful, slightly raspy tone is enveloped in Lang's molten silk as the two invite one another to "Say nighty-night and kiss me/ Just hold me tight and tell me you'll miss me." (RS)

"Steppin' Out With My Baby": The anticipation of a romantic night on the town brings out Bennett at his dandiest as he sings with giddy buoyancy. Written by Irving Berlin for Fred Astaire during the Golden Age of Hollywood, the song lilts and swings as Bennett dresses up for the evening "in my top hat and my white tie and my tails." (RS)

"The Best Is Yet to Come": When Bennett sings this ode to the glass half full, you get the feeling he's singing to himself. "We've only tasted the wine/ We're gonna drain the cup dry," he proclaims. It's hard to argue with that kind of optimism, especially when it's coming from someone who's been around the block as many times as Tony Bennett. (RS)


"Nice and Slow": Lyrical subtlety is fine and good, but Usher—who starts this modern standard by talking dirty in his steamy phone-sex voice—scored his first No. 1 hit by getting real pervy. "I wanna do something freaky to you, babe," the Ush insists. Who among us can resist Usher's sexin'? (CJ)

"U Remind Me": "Thought that she was the one for me," Usher sings here of a past love who spurned him. "Till I found out she was on her creep/ She was sexing everyone but me." Ouch. We're sure Usher's washboard abs and golden voice will lead him to a new boo, but the pain persists nonetheless. (CJ)

"Hey Daddy (Daddy's Home)": This airy 2009 ode to sexin' is perhaps the most redundantly titled and unintentionally creepy tune in Ush's repertoire. Even Usher's gorgeous, scale-climbing vocals can't erase the ew factor of "Daddy's" insistence that "it's time to play," and his subsequent request to "poke that bottom up in the air." (CJ)

"Love in This Club": Just when you thought Usher had done taken his sexual conquests to every frontier, he suggests the most disturbing location to sex a girl to date: In the middle of a dance club. Still, this synth jam—which involves much thrusting in live performance—was the most infectious hit 2009 had to offer. Again, we have no choice but to submit to Usher's sexing. (CJ) 

SEE IT: Usher plays the Rose Garden Arena on Thursday, May 26, at 8 pm. $29.50-$99.50. Tony Bennett plays the Arlene Schnitzer Concert Hall on Friday, May 27. 7:30 pm. $55-$150. Both shows all ages.