■ The Pop Edition

October 23: iPod Launches at 25, Reynolds Turns 50

A pocket-sized music player rewired how we listened, a Canadian kid became a movie star, and Chicago ruled the airwaves — all on the same calendar square.

The white earbuds era began quietly in a San Francisco auditorium 25 years ago today.

October 23 splits its attention between a piece of hardware that changed how an entire generation carried its music and a run of birthdays that spans decades of pop culture range — from a Grammy-winning parody artist to a superhero-movie leading man. Add in a soft-rock chart-topper from the bicentennial year, and you've got a date that's less about one big bang and more about steady, lasting influence. Here's the full rundown.

Ryan Reynolds

BORN 1976 · TURNS 50

He spent years as the reliable charming guy in comedies nobody quite loved before Deadpool let him weaponize the smirk into a franchise. Since then he's built a second career as a marketing savant, turning a gin brand and a mobile carrier into punchlines that sell.

Emilia Clarke

BORN 1986 · TURNS 40

She was a working actress with a handful of small credits when Game of Thrones cast her as a teenager who inherits dragons and a claim to a throne. Eight seasons later she'd become one of the most recognizable faces on television, and has since moved into voice work and producing.

"Weird Al" Yankovic

BORN 1959 · TURNS 67

He started recording song parodies on an accordion in his college dorm and turned it into a five-decade career that's outlasted most of the artists he's spoofed. He's won multiple Grammys and remains the rare novelty act that critics take seriously.

Pelé

BORN 1940 · WOULD HAVE BEEN 86

He won three World Cups with Brazil and turned soccer into a global television spectacle decades before most of the world had a television. He died in 2022, but his highlight reels still circulate as the standard other players get measured against.

Dwight Yoakam

BORN 1956 · TURNS 70

He dragged honky-tonk twang back into the mainstream at a moment when country radio wanted polish, and did it his own way from Los Angeles rather than Nashville. He's since built a second career as a character actor in films like Sling Blade.

PRESS START: The iPod Arrives

Steve Jobs stood in a small auditorium at Apple's Cupertino campus on October 23, 2001, and pulled a white plastic device out of his jeans pocket. It held, he said, a thousand songs. That was the whole pitch, and it was enough.

The first-generation iPod cost $399, worked only with Macs, and used a mechanical scroll wheel that felt like nothing else on the market. Reviewers were cautiously impressed but skeptical of the price tag; sales were modest at first, and it took the 2003 arrival of Windows compatibility and the iTunes Store to turn the device into a phenomenon rather than a niche gadget for Mac loyalists.

What the iPod actually displaced was the Discman and the CD binder, and with them the entire ritual of carrying physical albums around. It also quietly rewired the music business, making the single, not the album, the default unit of consumption again — a shift that streaming later completed. Apple stopped selling the iPod entirely in 2022, by which point its job — proving people would buy music digitally, one song at a time — was long finished.

ON THE CHARTS: Chicago's Soft-Rock Peak

Chicago's "If You Leave Me Now" held the top of the Billboard Hot 100 through the week of October 23, 1976, capping a two-week run at number one for a band that had spent most of the decade known for horn-driven rock, not ballads.

The song marked a deliberate pivot. Chicago had scored plenty of hits earlier in the '70s, but this was their first number one, and it arrived stripped of the brass section that had defined the group — just Peter Cetera's vocal, strings, and a mid-tempo ache that fit perfectly between the disco and soft-rock lanes dominating 1976 radio. It also won the Grammy for Best Pop Vocal by a Duo or Group that year.

The success reoriented the band's whole approach for the rest of the decade, pushing them further toward ballads and away from the jazz-fusion instincts of their earlier records — a shift that some longtime fans grumbled about but that kept Chicago on the radio well into the 1980s.

Meanwhile…

1998Pleasantville opens in wide release, sending teenagers into a black-and-white 1950s sitcom world that gradually blooms into color.

1983Country singer Ronnie Milsap's run of chart-toppers continues to define Nashville's crossover pop sound of the era.

2001The same Apple event that unveils the iPod also marks one of the last times Steve Jobs keynotes a product launch without a global audience already expecting a hit.

1956Elvis Presley's early singles continue climbing the country and pop charts simultaneously, a crossover feat that was still rare at the time.

1976Chicago's ballad turn coincides with a broader shift on FM radio away from arena rock and toward smoother, string-laden production.

2015Crimson Peak opens in theaters, giving Guillermo del Toro's gothic sensibilities a big-budget studio showcase.

From a scroll wheel that reshaped the music industry to a ballad that reshaped a band's whole identity, October 23 is a reminder that quiet pivots often outlast the loud ones. Check back tomorrow for another day's worth.