A few weeks ago—when Norah Jones, Rosanne Cash, John Mellencamp, and Kris Krisofferson visited SPECTACLE—we looked at Elvis Costello’s relationship to American music. We set aside jazz, though, for this week. And there is perhaps no single figure that better represents the range and possibilities of jazz than Herbie Hancock, this week’s guest. Over the years, Hancock has helped shape the direction of post-bop modern jazz through his work with Miles Davis; played a fundamental role in the development of hip-hop with the groundbreaking hit “Rockit”; and expanded the potential for funk with his band, the Headhunters.

Though he has often received criticism, or at least a good degree of confusion, for his eclectic approach, Hancock has always argued that these styles all fit squarely into the evolving tradition of improvisational music. Though hardly a jazz virtuoso, Elvis has also consistently, if infrequently, explored different aspects of jazz in his own music.

If there is one song that secured Elvis a spot in the jazz tradition, it is “Almost Blue,” from the 1982 album Imperial Bedroom. Though the song shares its title with the album of country covers that Costello recorded the previous year, it actually came directly out of the torch song tradition, and was later recorded by (among many others) one of its actual inspirations, the smoldering “cool jazz” singer and trumpeter Chet Baker.

He would experiment with more jazz-oriented songs over the years, like the version of Mose Allison’s “Everybody’s Crying Mercy” included on the Kojak Variety album. Elvis’s biggest step into improvisational music came after he served as artistic chair for the 1995 Meltdown Festival; jazz guitarist Bill Frisell was part of the event, which led to the two of them collaborating on an EP titled Deep Dead Blue. (The friendship with Frisell continues—the guitarist has turned up on several episodes of SPECTACLE.)

A jazz feel figured prominently in Il Sogno, Elvis’s 2004 orchestral work. His next major project, however, started a year earlier, when he paid a visit to legendary pianist Marian McPartland’s National Public Radio show, Piano Jazz. The two British musicians performed a mix of standards and Costello originals; the results were released on a 2005 CD.

Of course, the most ongoing relationship that Elvis has with the jazz world is his marriage to pianist and singer Diana Krall, one of the world’s most popular jazz musicians. Her 2004 album, The Girl in the Other Room, consisted mostly of songs that the couple co-wrote—though, just to bring things full circle, it also included her version of “Almost Blue.” But if you want to hear more about Elvis and Diana…well, you’ll have to stick with SPECTACLE for a few more weeks.

– Alan Light

Alan Light is the former Editor-in-Chief of Spin and Vibe magazines, and a former Senior Writer for Rolling Stone. A frequent contributor to the New York Times, he is the author of “The Skills to Pay the Bills: The Story of the Beastie Boys” and a two-time winner of the ASCAP-Deems Taylor award for excellence in music writing.

This week’s guest on SPECTACLE, Rufus Wainwright, is one of the most acclaimed songwriters of his generation. He is equally celebrated, however, for his power as a live performer; as he notes in the episode, he’s been on stage from a very young age, singing with his mother and aunt, the renowned folksingers the McGarrigle Sisters. Wainwright has performed in a wide range of settings, as a pure solo act and backed by an orchestra, culminating in his 2006 recreation of Judy Garland’s 1961 Carnegie Hall concert, which was released as the Grammy-nominated album Rufus Does Judy at Carnegie Hall.

Elvis Costello has also performed and toured in a remarkable variety of configurations during a career that has now entered in fourth decade. Shockingly, though, he has never released a true, stand-alone live album—perhaps because his material and arrangements change so rapidly from year to year and from tour to tour. He has issued live recordings of collaborations with such artists as jazz pianist Marian McPartland, guitarist Bill Frisell, and the Metropole Orkest, but never a straight-up rock & roll concert. (To be fair, the expanded reissues of most of Elvis’s catalogue include live tracks captured over the years, and the widely-bootlegged 1978 promotional album, Live at the El Mocambo, was legally issued in 1993, but only as a bonus to an anthology set.)

For almost twenty years, the faithful Attractions provided accompaniment for Elvis on stage as well as on vinyl—though he first “disbanded” the group as far back as 1984. At Live Aid in 1985, he was told that because of time constraints, he should “ditch the band,” and he sang “All You Need is Love” alone with an acoustic guitar. When he brought back the Attractions for part of the 1986 King of America album, the resulting tour reflected his uncertain allegiances—and produced some of his finest shows. Each city was a three-night stand: one show with the Attractions; one with the rootsier outfit known as the Confederates, featuring former Elvis Presley guitarist James Burton; and one night as a solo act.

The follow-up album, Blood and Chocolate, spawned a tour in which Elvis hosted the evening as the unctuous MC Napoleon Dynamite, giving a vaudeville-style feel to a show that included a roulette wheel, spun to select the evening’s set list. After a series of more experimental releases, Elvis hit the road in 1996 for a run of club dates, backed only by Steve Nieve’s piano. A tour with the Attractions followed, which would be their last as a unit. In 2002, when he went out after the release of the When I Was Cruel album, his support came from the Imposters (with Davey Faragher replacing Bruce Thomas on bass), which has been his touring band ever since—except when he plays solo, as he did when opening for Bob Dylan in 2007.

Of course, some of Elvis’s greatest on-stage moments were broadcast on television, including his legendary switch from “Less Than Zero” to “Radio Radio” on Saturday Night Live in 1977. And if you’ve never had the pleasure of seeing the man perform, there’s this new show on the Sundance Channel you might want to check out…

– Alan Light

Alan Light is the former Editor-in-Chief of Spin and Vibe magazines, and a former Senior Writer for Rolling Stone. A frequent contributor to the New York Times, he is the author of “The Skills to Pay the Bills: The Story of the Beastie Boys” and a two-time winner of the ASCAP-Deems Taylor award for excellence in music writing.

This week’s guest on SPECTACLE, President Bill Clinton, is probably the single most defining figure of the 1990s. His election in 1992 marked the triumph of the Baby Boom generation on the global stage, and during his two terms in the White House, the United States enjoyed peace and unprecedented prosperity; the record federal budget deficit that he inherited had been turned into the largest surplus in history by the time he left office in 2001.

For Elvis Costello, though, the ‘90s weren’t a placid time—his decade was most notable for a boundless sense of musical exploration. Through the ‘70s and ‘80s, Elvis was unarguably a rock artist, occasionally (and increasingly) experimenting with more traditional pop and roots song forms. His first release of the new decade, 1991’s Mighty Like a Rose, remained squarely in that territory. But in 1993, Elvis took his biggest creative leap yet, collaborating with the Brodsky Quartet on a classical song cycle based on the Romeo and Juliet story, titled The Juliet Letters.

The following year, Brutal Youth reunited him with the Attractions (for the last time) for some full-on rock & roll, but he quickly veered off into other directions. Kojak Variety—released in 1995, but recorded several years earlier—was a collection of covers, while the next year’s follow-up, All This Useless Beauty, was a ballad-heavy set of songs originally intended for other artists.

Elvis’s newfound sense of sonic restlessness was perhaps best displayed when he curated the 1995 Meltdown Festival, presenting a slate of artists ranging from Jeff Buckley to the London Philharmonic to legendary street musician Moondog. (The festival initiated a friendship with jazz guitarist Bill Frisell, which later resulted in the album The Sweetest Punch). The ‘90s ended on a high note, the acclaimed, Grammy-winning 1998 collaboration with Burt Bacharach, Painted from Memory.

– Alan Light

Alan Light is the former Editor-in-Chief of Spin and Vibe magazines, and a former Senior Writer for Rolling Stone. A frequent contributor to the New York Times, he is the author of “The Skills to Pay the Bills: The Story of the Beastie Boys” and a two-time winner of the ASCAP-Deems Taylor award for excellence in music writing.

Unpredictably, the 1990s also saw Elvis involved with film on a consistent basis. He began the decade co-composing the mostly orchestral score for the British mini-series G.B.H., which starred Michael Palin from Monty Python’s Flying Circus. Elvis and Bacharach first worked together on the song “God Give Me Strength,” from the 1996 movie Grace of My Heart; the unlikely duo also showed up in Austin Powers: The Spy Who Shagged Me, singing “I’ll Never Fall in Love Again.”

Even sillier, Elvis appeared as himself in Spice World and the ‘80s nostalgia film 200 Cigarettes. He also wrote “I Throw My Toys Around” for The Rugrats Movie, performing it with No Doubt, and contributed a version of the standard “She” to the 1999 soundtrack of Notting Hill. By now, it was clear that Elvis Costello could no longer be defined as a rocker, or even exclusively as a musician. It was the end of the century, and all bets were off.

– Alan Light

Alan Light is the former Editor-in-Chief of Spin and Vibe magazines, and a former Senior Writer for Rolling Stone. A frequent contributor to the New York Times, he is the author of “The Skills to Pay the Bills: The Story of the Beastie Boys” and a two-time winner of the ASCAP-Deems Taylor award for excellence in music writing.