Whenever former child actor Fred Savage runs into fans of “The Wonder Years,” the TV series from the late 1980s about coming of age in the late 1960s, they almost always say the same thing.

“They ask, ‘How’s Winnie?’” says Mr. Savage, now a 38-year-old TV director, invoking his character Kevin Arnold’s first love. “And they ask, ‘When is the show coming out on DVD?’”

After more than 20 years off the air—and a boom in the DVD market that came and went—the complete “Wonder Years” is finally being released Tuesday. A limited edition of the DVD set, packaged in a miniature school locker with a yearbook signed by cast members, sells for $500. (The basic set starts at $250). It’s a five-pound, 26-disc example of how the entertainment industry tries to monetize long-dormant properties, gambling on how deeply they still resonate with fans.

Nostalgia is a powerful marketing force, and “The Wonder Years” manages to evoke multiple eras. But it’s unclear whether fans’ enduring affection for the show will outweigh the generally fading appeal of buying DVDs. Indeed, the series has long been available for online streaming but as an altered (unwatchable, some die-hard fans argue) version from the original.

The 1980s TV show starring, from left, Josh Saviano, Fred Savage and Danica McKellar, will be released on DVD. ABC/Getty Images

The long road to DVD for “The Wonder Years” shows how complex and expensive rights issues can stymie a release despite high demand. It turns out the very music that helped make the show so pioneering ended up being the culprit in keeping it in video purgatory—costing owner Twentieth Century Fox Television a bundle of lost DVD revenue. Songs by the likes of Bob Dylan, Jimi Hendrix and the Beach Boys contributed to the show’s crossover appeal among nostalgic baby boomers and their Gen X kids, many of whom were just discovering those vintage hits. But those songs, including the evocative theme music, Joe Cocker’s rendition of the Beatles’ “With a Little Help From My Friends,” had only been licensed for the show’s initial broadcast run.

At the time, it was easier and cheaper for the studio to secure permissions for the short term. And there wasn’t much of an afterlife for TV series on videocassette. Demand for such DVD collections eventually surged, but by then the potential costs of licensing all the marquee tunes in “The Wonder Years” scared distributors off. That’s why so many of the original songs went missing from the streaming version on Netflix. NFLX +2.12%

“We had no idea at the time that these great songs would be the thing that kept ‘The Wonder Years’ from the fans,” says Danica McKellar, who played Winnie Cooper. (By the way, she’s doing fine, thanks. She published several books about math for young readers, competed on “Dancing With the Stars,” and was recently hired as a game-show host.)

“The Wonder Years” premiered on ABC after the 1988 Super Bowl, “a bit of Americana after the quintessential example of Americana,” recalls Neal Marlens, who created the series with his wife, Carol Black. It performed well in the ratings, but was less than a smash. However, the show was an immediate hit with critics, and won the Emmy for outstanding comedy after its first season of just six episodes.

The story was told from two perspectives: As 12-year-old Kevin Arnold navigated school pressures, family politics and a crush on the girl next door (while wearing his trademark New York Jets jacket), his older self reflected sagely on those experiences through the narration of actor Daniel Stern.

Big events from America’s collective memory, such as the moon landing, often provided a framework for the episodes. But it was the lens on average, suburban life—the luster of a new family car, sports tryouts, dealing with a bully—that made the show ring true for many viewers. That included people who were born after the ’60s, or those who only experienced Woodstock by listening to the record, if at all.

Mr. Marlens and Ms. Black, who were coming off a hit comedy he had created, “Growing Pains,” modeled the Arnold family’s home after the nearly identical houses of their youths—his in Huntington, N.Y., and hers in Silver Spring, M.D., in new subdivisions where the trees were still small.

They scoured Los Angeles for a neighborhood that looked generically American (no palm trees) and finally found a location in Burbank, on a street where saplings had recently replaced older trees wiped out in a blight. Interior shots were filmed on stages built in a warehouse in Culver City, far from the big studio lots.

The young cast, including Josh Saviano as Kevin’s geeky buddy Paul, revolved around Fred Savage. He was from Chicago and, like his young co-stars, only had a few credits to his name. During shoots, there were always two cameras trained on Mr. Savage. Producers needed as much footage as possible because of the limits on work hours for child actors. More important, Kevin Arnold was at the core of every episode, allowing viewers to watch the character (and the actor who played him) grow up in real time.

“Sometimes Kevin was a little ahead of me in his experiences, sometimes I was ahead in real life, but there were definitely a lot of parallels,” Mr. Savage recalls, without offering specifics from his adolescence. “It was very helpful, like having a dry run.”

Like many of the kids watching him on screen, Mr. Savage had his music tastes shaped by “The Wonder Years.” Kirk Trutner, an actor whose job involved reading the narration in the script so the actors could hear it on set, made mixtapes for the tween actor that featured Bob Dylan, James Taylor and the Grateful Dead. “He and my dad probably had the biggest impact on the music I listen to today,” says Mr. Savage, who has three young kids of his own.

Fred Savage and Danica McKellar as pre-teens in season one of ‘The Wonder Years’ ABC/Getty Images

Songs for the show were typically chosen during the editing process. Bob Brush, who ran the show after Mr. Marlens and Ms. Black left during its second season, would send runners to fetch cassettes from a nearby record store, then play the tapes on a boombox in his office as he and his staff members searched for the best song to underscore a scene.

Most artists were happy to have their songs highlighted in the show. Others were tougher to pin down. Neil Young repeatedly denied requests to use his song “Long May You Run” in an episode about the Arnolds buying a new car. Producers say the singer changed his mind after they made a donation to a school for disabled children co-founded by Mr. Young’s wife.

Not every musical moment succeeded. For an episode in which Kevin starts a band, the TV studio that produced the series spent up to $75,000 to license an excerpt of the Beatles’ performance on “The Ed Sullivan Show.” Mr. Brush had asked for the footage so “The Wonder Years” could tell “the definitive story” of rock ’n’ roll’s big bang.

It wasn’t. The story of Kevin’s garage band, the Electric Shoes, didn’t live up to the Beatles buildup, Mr. Brush admits. “That was just a little hubris and overreach on our part.” After the episode aired, the head of studio New World Television, Jon Feltheimer (now chief executive of Lions Gate Entertainment), walked into Mr. Brush’s office and joked, “I want my money back.”

Home-video distributor Time Life spent two years preparing the show’s DVD release. The company’s deal with series owner Fox (which had acquired original owner New World), hinged on whether Time Life could secure the rights to the Joe Cocker theme song.

“If we couldn’t clear that song, there was no reason to go onward,” says Jeffrey Peisch, who runs Time Life’s video and music division.

He says the company spent a seven-figure sum to clear the theme song and 284 others for the DVD release—96% of the original music.

Mr. Peisch predicts the “Wonder Years” set will be profitable. “The audience of aging baby boomers are being ignored by many distributors, and people in this category still want to own product,” he says.

In the version of “The Wonder Years” streaming on Netflix, the first thing that greets viewers is a facsimile of the Joe Cocker theme, which had been swapped for a version performed by an uncredited singer. It was one of many music replacements throughout that caused core fans to reject the show’s altered form.

“I never dared to watch it with the music replaced,” Mr. Brush says. “It was if they had Photoshopped a new character in, or taken Kevin Arnold out.”

Knowing that the music would be a deal-breaker for potential buyers, Time Life made the unusual move of announcing the 14 songs it had failed to clear for the DVD release. That list (posted on the site TVShowsOnDVD.com) included songs by the Doors and Neil Young’s “Long May You Run.” Time Life, known for its old-fashioned TV infomercials, is promoting “The Wonder Years” with a commercial featuring a list of songs that scrolls up the screen.

Of course, the DVD release represents much more than a jukebox of famous songs for the cast and creators who remember “The Wonder Years” as a career highlight, one with a bittersweet ending.

When the show entered its sixth and final season, Mr. Savage was 16 years old. The running joke on set was that his character’s voice would soon be deeper than the narrator’s. The writers faced a growing challenge: how to reckon with puberty and surly teen behavior in a character who had begun as a sweet, smart-aleck kid.

Ken Topolsky, a producer on the show, says, “When it’s a suburban kid who has a pretty good life and he’s complaining about mom not letting him do something, you just want to smack him. That’s when we felt that Kevin’s wonder years were over.”

In an effort to find a new tone, the producer commissioned a “Wonder Years” script from David Chase, who was about six years from launching “The Sopranos” on HBO. His script was “phenomenal, one of the best,” Mr. Topolsky recalls, but the plot involved hard drug use and would have jarred the show.

Meanwhile, in the real world, the riots that engulfed L.A. in 1992 after the Rodney King beating presented an unwelcome flashback to the civil rights violence of the ’60s. On the music front, the blistering rock of Nirvana was breaking out, while “The Wonder Years” was showcasing Joni Mitchell and the Four Seasons.

Knowing that their chances of being renewed for another season were iffy, the producers decided to wrap up the show. The last episode aired in May of 1993. Set 20 years earlier, the two-part finale revolves around summer jobs at a resort, hitch hiking, a fistfight, and a Fourth of July parade. To escape a storm Kevin and Winnie dash into a barn, where they confront an inevitable breakup and, presumably, consummate their relationship.

Mr. Brush, who wrote the last episode, says, “Kevin had to get out of the house and become a man.”

Write to John Jurgensen at john.jurgensen@wsj.com