Sooner or later, critically and commercially successful musical performers face perplexing, exasperating decisions. When the prospect of legacy-act status looms, do they spend the remainder of their working lives just repeating their familiar hits for the fans they already have? Or do they try, instead, to keep right on creating new material that their longtime followers—let alone new, younger ones—might well find disappointing if different?

In early 1997, 21 years into their celebrated roots-rock career, Tom Petty and the Heartbreakers—creativity intact but tired of headlining arena-sized shows and of playing the same setlist nightly—came up with a third way. They arranged a booking at San Francisco’s storied, thousand-seat Fillmore auditorium and for 20 shows played whatever they felt like—mainly music that had excited and influenced them in the first place—70-plus numbers as diverse as those influences had been. Petty and company faced no pressure to come up with a new album just then, but recordings of a half-dozen of those shows are the basis, a quarter of a century later, of the constantly charming and surprising new set “Live at the Fillmore, 1997” (Warner, Nov. 25).

The album features the classic Heartbreakers lineup of Mike Campbell on lead and rhythm guitar (trading off those roles with Petty himself, depending on the song), Benmont Tench on keyboards, Howie Epstein on bass, Steve Ferrone on percussion and, at times, Scott Thurston on additional guitar. Both their full-band records and Petty’s solo outings were often pegged as “Southern Rock”; the sweeping range of flavors and songs here offers some insight into how that nebulous term applied to this outfit—and what it would play, given free rein.

The genres include country and country rock, soul, blues, pop, first-generation and British Invasion rock ’n’ roll, and even bluegrass. That enables, for example, an ingenious segue from a light, harmonica-driven summer-camp-style singalong on “You Are My Sunshine” into a pained, dark take on Bill Withers’s “Ain’t No Sunshine.”

Petty at the Fillmore in 1997Photo: Martyn Atkins

That the choices made are an identifying statement is underscored by two guest appearances: Roger McGuinn of the Byrds—who Petty sometimes resembled vocally and whom he calls his mentor here—joins in for a brotherly sounding close harmony duet on “It Won’t Be Wrong,” and on the soaring guitars of “Eight Miles High.” Elemental blues singer John Lee Hooker provides an expansive version of “Boogie Chillen” and Ray Charles’s “I Got a Woman.” Extended blues numbers, not a typical part of Heartbreakers live shows or records, are a rare side trip taken.

It’s not easy to bring the atmosphere of anybody’s favorite hometown bar into a bigger place, even of this moderately large size, but it gets done here. (The deluxe versions of the CD and vinyl sets include an embroidered jeans patch emblazoned “the fillmore house band.”) Endearingly, as your local cover band might, Petty and company play their favorite hit-record versions of classic songs with terrific exuberance—the Everly Brothers’ distinctive turn on Little Richard’s “Lucille”; the Rolling Stones’ hit versions of Irma Thomas’s “Time Is on My Side” and Chuck Berry’s “Around and Around”; and the Ventures’ rocking instrumental turn on Richard Rodgers’s 1930s ballet music, “Slaughter on 10th Avenue.”

It will not shock anybody that Tom Petty, born in 1950, would include a good many rockers from the early ’60s, just as he was coming of age, including the practically inevitable “Louie Louie” and “Gloria,” or that hot instrumentals, ranging from Booker T. & the M.G.’s “Green Onions” to John Barry’s Bond theme “Goldfinger” and country-artist Arthur Smith’s “Guitar Boogie Shuffle,” are saluted and played with expertise and gusto. The personal record collections of Petty and the Heartbreakers get a workout here, but nothing ever sounds by-the-numbers. Tom Petty and the Heartbreakers had a particular and uncommon facility for making chestnuts sound as fresh as their own material. At their best, as here, they are rhythmically tight, and the instrumentation and vocals are at once remindful of all those influences and immediately recognizable as their own.

And, yes, some of their own lasting hits show up at strategic points throughout both the 2-CD or 3-LP and extended deluxe sets—“American Girl” and “Free Fallin’,” “Even the Losers” and “You Don’t Know How It Feels.” They feel, in fact, right at home amid the music these beloved gents loved themselves.