Bruce Springsteen and the E Street Band performed just a handful of new songs in the tour that reached the U.S. in the summer of 1999. That year, he debuted the “secular gospel” of “The Land of Hope and Dreams,” now an unintended requiem for the last century’s final era of irresponsible innocence.

“Well, you don’t know where you’re goin’ now,” Springsteen sang, “but you know you won’t be back.”

That year’s winter troubles were in the rear-view; the failed impeachment of President Clinton had finally concluded, and Columbine was surely a one-off horror. The Summer of 1999 presented no worries, not in any intensity that mattered. May to September was a time to take nothing seriously, to simply enjoy summer days that were vapid and ridiculous, innovative and exciting. Like the long-dead refugees from the Roaring ‘20s, we didn’t know it may never be that good again.

Three new books explore aspects of the late ’90s, but converge most notably in that last great summer of 1999. By themselves they may seem light minutia, but together they capture the era’s buoyant—though irrational and ephemeral—exuberance.

Pedro tells the story of the era’s greatest baseball pitcher, Pedro Martinez, who had a spectacular ’99 season for the Boston Red Sox. He won 26 games across the regular season and playoffs, a career-high victory total.

That same summer, just miles away from Fenway Park, Shawn Fanning went live with Napster from his Northeastern College dorm room. But as Stephen Witt details in How Music Got Free, Napster was simply a platform: the audio compression file format it exploited represented the true revolution.

The Dow Jones index reached 11,000 for the first time that May and everyone was getting on board the unstoppable economic train. And those who couldn’t play the stock market could invest in plush stuffed animals, a desperate dream explored in Zac Bissonnette’s The Great Beanie Baby Bubble.

Summer 1999 was full of portent. Osama Bin Laden was added to the FBI’s Most Wanted List in June. Days later, George W. Bush announced for president. In July, Lance Armstrong won his first Tour De France and The Sopranos first season earned 16 Emmy nominations. That August, “I see dead people” and The Blair Witch Project were added to the cultural consciousness.

It would be such a summer.

In every way that mattered, the Summer of 1999 began at Fenway Park, on the evening of May 18, 1999, with Pedro Martinez throwing 11 strikeouts against the defending world champion New York Yankees—his seventh game in a row with more than 10 Ks.

Ninety minutes after Martinez earned that win in a 6-3 Red Sox victory, East Coast movie fans caught midnight shows of the first new Star Wars movie in 16 years: The Phantom Menace. The film’s opening crawl (“The taxation of trade routes to outlying star systems is in dispute. Hoping to resolve the matter with a blockade … the greedy Trade Federation has stopped all shipping to the small planet of Naboo”) set a strange tone for an action/sci-fi movie, and the initial reviews were tepid. Nonetheless, the movie went on to gross $900 million worldwide. After a decade surprisingly short on sequels, The Phantom Menace reversed the trend: Hollywood would spend the first years of the new century exploiting the financial successes of one stable, ongoing movie franchise after another.

Earlier that same May 18, Bruce Springsteen had announced the first U.S. dates of that summer’s reunion tour of the E Street Band—their first tour in 10 years. Five shows in New Jersey would eventually balloon into 15 New Jersey dates through July and August in a tour that ultimately stretched to July 2000. It was a testament to Springsteen’s drawing power as a live performer that his tour supported no corresponding music release. Britney Spears, in contrast, began her first headlining tour on June 28 in direct support of her debut album, …Baby One More Time, released that January. According to Billboard sales charts, the album had sold four million copies as of May 24; supported by the tour, it would sell 10 million units by the end of the year.

CD sales were everything, Witt writes in How Music Got Free. After a merger with Polygram, Universal Music Group would pull in $6 billion in revenue during 1999. Universal could produce half-a-million CDs a day at a per-unit cost of less than a dollar, “a savings that was not passed on to the customer,” who paid a peak average of $14 per CD. Further, Witt writes, the Big Five music distributors colluded with stores like Tower Records and Musicland to discourage any discounts. The cost of this blockade—this taxation of trade routes, as it were—gained the record industry an estimated $.5 billion from 1995-2000, “two bucks from the pocket of every American.”

“Consolidation in the radio industry also helped,” Witt writes, “creating a homogeneous listening environment that could propel an album to platinum status on the basis of a single hit.”

After all, consumers had to buy the entire album.

When Polygram and Universal had first begun their merger talks, Witt writes, the prospectus examined by Universal chairman Doug Morris spent time on the benefits of absorbing Polygram’s huge CD production plant in Tennessee. It mentioned risks of CD bootlegging, similar to the tape-to-tape copying that Alan Greenspan had warned, in 1982, might require aggressive law enforcement to forestall.

But this sort of bootlegging was unwieldy. Computer processers and CD burners of the time were slow, Witt writes, and could take six hours to audio-rip a CD into a file, and then take another hour to make a CD copy—not a tenable means of large-scale bootlegging.

Consequently, the merger prospectus “did not mention the personal computer, nor recent advancements in audio compression technology. It did not mention the potential for file sharing. And it did not mention the MP3.”

On June 1, 1999, Shawn Fanning went live with Napster from his Northeastern dorm room. While Napster’s peer-to-peer file-sharing platform got most of the attention in years to come, often overlooked was what Witt calls the truly game-changing technological innovation: the MP3 file. The music industry’s unwillingness to be first-adopters doomed what seemed to be its unstoppable growth.

Witt’s narrative delves into technical minutia, but never so deeply that it’s difficult to understand. He organizes his narrative around alternating chapters that each focus on a separate protagonist: an engineer, an executive, and a criminal: Universal chairman Doug Morris and two nemeses Morris didn’t even know he had: German engineer Karlheinz Brandenburg, and music pirate Dell Glover, a Polygram/Universal employee at the Tennessee CD manufacturing plant.

Brandenburg and the rest of his engineering team perfected the compressed sound quality of the MP3, a small enough file to transfer. That breakthrough enabled pirates like Glover to smuggle CDs from the production floor, rip and share them to the Internet Relay Chat “dark rooms” of cyberspace.

Before Napster, music pirates were already sharing cracked MP3 files by the thousands. Napster provided the critical tipping point of ease-of-use. Even after Napster was out of business, the now tens-of-millions of MP3 files would motivate the development of MP3 players. By the summer of 1999, the CD’s era had begun its rapid fade, and so had the music industry’s enormous profit margins.

Music stopped being a product built around an album of songs, shifting to a high-priced, luxury concert experience.

“From 1999 to 2009 concert ticket sales in North America more than tripled,” Witt writes. “Many musicians began to earn more by touring than recording.” In 1997, ticket prices for the Rolling Stones stadium tour topped out at $60 for the best seats on the field; in 2002, they were $350. Britney Spears’s 1999-2000 tour grossed $35 million; her 2009 tour grossed $131 million. Bruce Springsteen would tour again in 2002, this time with a CD release—The Rising—to promote. The title track, about New York City firemen, was first streamed on America Online; according to E!Online it was quickly cracked and traded as an MP3. By 2007, Springsteen’s single “Radio Nowhere” was released as a free download right from the start, in advance of the release of the album Magic.

Not all business people were as clueless as those in the music industry when it came to understanding—and manipulating—the shattering changes brought by the Internet: Ty Warner’s stuffed, plush Beanie Babies used the web to facilitate an eBay-driven obsession with stuffed animals bought and sold for ever-increasing prices. By 1998, 64 percent of Americans owned at least one Beanie Baby, according to Zac Bissonnette in The Great Beanie Baby Bubble. The fad was so lucrative that early in 1999 Ty Warner gave his 300 employees at Ty Inc. bonuses equivalent to their entire 1998 salaries.

Bissonnette ably investigates the “niche history” of Beanie Babies, a fad that perfectly encapsulates the irrational exuberance of the era. His anecdote-driven narrative portrays not only the desperate collectors but also peers into the strange creative mind of the man behind the craze: Ty Warner, a deeply-flawed but brilliant man. The micro-economy that grew up around Beanie Babies was magnified, and then destroyed, as the Internet allowed the hobby to grow and spread. The book successfully shows the razor’s edge of responsible economic behavior shifting to risk, then madness.

That exuberance was helped by Warner’s fiercely-protected marketing of his Beanie Babies, which helped make his product seem exclusive. One marketing deal that he did permit was with Major League Baseball.

Pedro Martinez’s May victory against the Yankees came on the one-year anniversary of a May 18, 1998, Chicago Cubs Beanie Babies giveaway that spiked attendance from fewer than 20,000 fans to 37,958. The Cubs said it was the biggest driver for attendance since Wrigley Field’s first-ever night game in 1988.

Major League Baseball distributed “Glory the Bear” at the 1998 All-Star Game in Denver’s Coors Field. According to Newsweek, post-game deals for “Glory” spiked to $150. Now they sell on eBay for $3. The bottom would drop out. It always does.

Ty Warner, to his credit, never changed the Beanie Baby pricing model, Bissonnette explains. He wholesaled the toys for $2.50 each, and retailers were expected to charge $5. But Warner did manipulate the market with cagey and surprising announcements of “retirements,” driving up collector demand for supposedly limited items. But there was no limit—the stuffed animals were being produced by the millions in Chinese factories. Bissonnette explains Warner’s business model of tight control of distribution: no Wal-Mart or other big box toy stores. Beanie Babies only seemed hard to find.

By May 1999, Bissonnette writes, “there were more than 79,000 items listed in eBay’s ‘beanbag plush’ category—triple-digit growth over the past couple years that was rapidly outpacing the growth in sales of Beanies on the primary market” of toy stores. Just as the Internet had driven up interest, allowing housewives to collect, speculate, and sell ever-more-valuable Beanie Babies like “Glory the Bear,” eBay provided transparency about the true inventory.

The mammoth inventory on eBay was not a harbinger of growing interest, it was the dump at the crash. The first McDonald’s promotion, a $100 million deal in 1997, featured nonstop crowds, constant phone calls and questions about inventory, and garbage cans full of discarded hamburgers—Happy Meals were bought just for the toy inside. By the third McDonald’s promotion in 1999, “there were no lines.”

Sensing the waning interest in his product, Ty Warner angled for one more big payout from the Beanie Babies. On August 31, 1999, he announced the Babies complete retirement, with the final bear, “The End,” released on December 31. It was a ploy—Warner would offer a fan vote to bring the toys back, but after a brief surge of interest, nobody cared. By late 2000, the toys had begun appearing at the discount stores that Warner had desperately tried to avoid, sold in bulk by toy stores stuck with inventory. They were just cheap junk, in obvious oversupply.

Transparency, Bissonnette compellingly shows, kills an item like Beanie Babies, eliminating the prestige factor of ownership when everybody can have it with no effort. In contrast, intangibles like music are meant to be shared—discussion and mutual enthusiasm are what drive interest.

Music sales used to work on a simple equation: “After hearing that great song on the radio, people went out and bought the entire album on CD. But now the last step was broken,” Witt writes. “There had been a time when artists had embraced the album [but] for the last 20 years, music had been a hits-first business.” By 2006, Witt writes, the music industry resembled the pre-album 45 rpm vinyl single days of 1963. But as with Beanie Babies, what the Internet took away, it also gave. With all that digital freedom, and minus the 74-minute storage restriction of the CD, “Why not just put out some songs?”

So in the Summer of 2015, music is all about singles and Internet buzz; Beanie Babies are kitschy junk; Pedro Martinez is going into the Hall of Fame.

Pedro’s last summer moment of 1999 occurred in a Septmber game against the New York Yankees—a 17-strikeout (most ever against the Yankees), one-hit performance. In October, Boston would lose the American League Championship Series to those Yankees, a dynasty that would win two more World Series; by the time the Red Sox reached the playoffs again, in 2003, the world had very much changed. Summer ended with Pedro’s last pitch, on September 10, 1999.

The summer of 2000 was consumed in the acrimony of the presidential election; 2001’s by Enron scandal and the end of the DotCom stock bubble. Then it wasn’t summer anymore.

But back on May 18, 1999, it was a perfect 69 degrees when Pedro Martinez took the mound at 7:06 p.m. Bruce Springsteen and the E Street Band were coming back and bringing Star Wars with them. We could invest in silly stuffed animals, and with some guiltless effort listen to music for free. Osama bin Laden was far away and on the run. Pedro would beat the Yankees that night and pitch the Red Sox, for a time, into first place in the American League East. It was the perfect start to summer. Absolutely perfect.

Nathan S. Webster reported several times from Iraq as a freelance photojournalist embedded with U.S. soldiers. He is currently a lecturer in English at the University of New Hampshire.