(December 30, 2025) – In 1995, many people were just discovering the Internet and its capabilities. By 2025, Billboard magazine was having to decide whether songs created with artificial intelligence and a few keystrokes should be allowed to populate its charts.
But that news was just one of many head-swiveling developments in 2025 that, 30 years earlier, no one could’ve fathomed. DJROBBLOG has captured a few here that might resonate with readers who were old enough to remember when MTV was so big that its then-parent company — Viacom — was actually considering starting or buying a record company. Now the once Music Television is reportedly shutting down all of its remaining dedicated music-only channels outside the U.S. by the end of 2025 due to declining viewership.
Here are some more of 2025’s WTF moments that no one in 1995 could’ve imagined happening.
Snoop’s Transformation
If someone had told me in 1995 that, in 30 years, we’d have gangsta rap kingpin Snoop Dogg introduced during a Christmas NFL game’s halftime show by home and hospitality mogul Martha Stewart and performing with Italian operatic pop singer Andrea Bocelli, alongside a popular country singer and a fictional trio of K-pop phenoms, my first question — after “what is K-pop?” — would’ve been, “are you sh-ttin’ me?”
You have to remember that, in December 1995, Snoop was still signed to — and still top dog at — Death Row Records, hip-hop’s then No. 1 gangsta rap label that had just signed Tupac Shakur and which was on the cusp of the infamous East vs. West beef with Sean “Diddy” Combs’ Bad Boy Records (in ‘95 I might have given that same WTF reaction to the name “Diddy”).
So the prospect of pup Snoop (still “Doggy Dogg” at the time), looking all grandfatherly on Christmas night while donning a Santa suit and holding court over Bocelli, country singer Lainey Wilson, and K-Pop’s 2025 breakthrough K-Pop trio HUNTR/X, is not one that I would have had on my bingo card 30 years ago.
But the 2025 version of Tha Doggfather, who has recently curried favor with the current White House occupant (who in 1995 saw that in Donald Trump’s future?), is easily among the most sanitized, most mainstream figures in hip-hop today. Age has a way of changing people, and in Snoop’s case he’s become a person who would be completely unrecognizable to those of us who recall his “Murder Was the Case” days (and the so-named charges he was fighting in ‘95 — and acquitted of in ‘96).
That evolution doesn’t erase who Snoop was — it just underscores how radically hip-hop’s relationship with power, branding, and respectability has shifted.
The Fall of Puffy, I Mean Diddy
But corresponding with Snoop’s ascendancy — he now owns and records for the recently revitalized Death Row, while its founder Suge Knight is serving a 28-year sentence for voluntary manslaughter — came the fall of Sean “Diddy” Combs. In 1995, the Bad Boy founder and future mogul was on his own climb to the top of the hip-hop heap. His rivalry with Knight, along with that of their two premier acts The Notorious B.I.G. and Shakur, respectively, hadn’t yet hit its crescendo. Diddy — Puffy at the time — was scoring big in ‘95 with hits by Biggie, Faith Evans, Total, as well as outside projects with Mary J. Blige and Lil Kim.
Fast forward 30 years, and not only is Diddy serving time for two prostitution transportation convictions this year, but it has been widely speculated — but never proven — that he was behind the unsolved murder of Shakur in 1996 as well as allegedly knowledgeable about who killed his own artist Biggie six months later. Both cases are nearing their 30th anniversaries and remain unsolved.
The Rise of Billionaires
In 1995, no musicians — not even Michael Jackson or Paul McCartney — had reached billionaire status. In 2025, the fifth has just been named by Forbes magazine: Beyoncé. In fact, of the five officially recognized by Forbes, only one had recorded music prior to 1995: rocker Bruce Springsteen. According to Forbes, The Boss has attained at least $1B in net worth and has been joined by a rapper — Jay-Z — and three women: Rihanna, Taylor Swift and now Queen B, none of whom had their first professional recording until Jay-Z’s 1996 debut with Foxy Brown (“Ain’t No Nigga”). While Forbes has disputed this, McCartney and Kanye West — on and off again — have been given billionaire status in recent years.
In 1995, success was measured in hits and tours; by 2025, it’s measured in ownership, branding, and financial leverage.
Never Say Never Until Now
The alt-rock band Jane’s Addiction’s history has been, well, characterized by addictive tendencies. They have disbanded and reunited more times over their 40 year history than a junkie and his crack pipe. But the latest and seemingly final breakup for the group who is still best known for its 1990 hit, “Been Caught Stealing,” became official in December 2025 after vocalist Perry Farrell settled lawsuits with his former bandmates Dave Navarro, Eric Avery, and Stephen Perkins, following a violent altercation between Farrell and Navarro that abruptly ended a September 2024 concert in Boston. That show was to be part of a planned reunion tour for The Lollapalooza founders that would carry them into 2025 and possibly include new music. Instead, it appears the group has said its final goodbye to fans via separate statements from Farrell and (jointly) his three ex-bandmates, and their last show will forever be that one in Boston where Farrell allegedly assaulted Navarro and ended a 40-year association in the process.
Already broken up once and several years removed from their biggest hits, I’d have never predicted in 1995 that Jane’s Addiction would be headline news — and for the above reasons — in 2025.
What in the Holly Jolly Heck is Happening?
When 1960s pop crooner Dean Martin passed away on Christmas Day 1995, it was noted then that he was one of only a handful of male acts (and no females) who’d accomplished the rare feat of having No. 1 records before and after the Beatles first dominated the charts in 1964. Since then, not only has a woman — Brenda Lee who topped the charts twice in 1960 and again in 2023 — been added to that pre-and post-Beatles list, but both Lee and Martin are now part of the annual holiday tradition of top charting hits on the Hot 100 with their “Rockin’ Around the Christmas Tree” and “Let It Snow! Let It Snow! Let It Snow!,” respectively.
In fact, the top half of the latest Hot 100 (Jan. 3) consists of 46 holiday tunes. That’s remarkable when one considers there were only two such songs in the top 50 of Hot 100 Airplay during the 1995 season: Mariah Carey’s then-one-year-old “All I Want for Christmas Is You” at No. 35, and Adam Sandler’s then-new parody hit, “The Chanukah Song,” at No. 10.
What once felt like a novelty chart quirk has now become a structural reality of the streaming era (cue the 1995 me: “Streaming? What is streaming!?”).
Mariah Was Tops Then and Tops Now
In 1995, Mariah Carey, whose Christmas anthem played second fiddle to her contemporary hits back then, was in the midst of a record-setting 16-week run at No. 1 with “One Sweet Day” (w/ Boyz II Men). She has now reclaimed the record with “All I Want For Christmas Is You,” which just capped its record-extending 22nd non-consecutive week at No. 1 (on the chart dated Jan. 3, reflecting activity during the week of Christmas). “All I Want,” whose No. 35 peak on Billboard’s Hot 100 airplay chart in 1995 certainly belied its future classic status, has now become THE Christmas standard to beat (and Mariah’s biggest hit). The scary part is that there appears to be no end in sight for the song that, by 2055, could still be the holiday standard bearer.
By the way, given the chart rules at the time, no one in 1995 would’ve predicted that, not only would “All I Want” be the record-holder for most weeks at No. 1 on the Hot 100, but that it would be Mariah’s 19th No. 1 single, placing her just one behind the Fab Four with 20 chart toppers.
Speaking of The Beatles…About That 30-Year Span
In 1995, I — like many other fans — was surprised when the former lads from Liverpool became one of only two acts who’d charted in 1965 to also do so exactly 30 years later. It happened first via a live cover of “Baby It’s You” that April and then again in December when “Free As a Bird” (featuring the then-three surviving Beatles backing a track originally recorded by John Lennon) entered the chart. The other 1965 chart veteran at that time was Stevie Wonder, whose “For Your Love” made it to No. 53 in ‘95.
Fast forward to 2025, and there were equally only two acts who’d reached the Hot 100 in 1995 who also did so this past year — both via songs that were recorded before ‘95. One was Mariah Carey, of course, with the return of her 1994 “Christmas” classic. The other, surprisingly, was Janet Jackson, who was featured on Cardi B’s “Principal,” a No. 92 entry this year that included a sample of Jackson’s “The Pleasure Principle” from 1986. It’s worth noting that several other acts who charted before 1995 also charted in 2025, but they were older recordings attributed to either holiday returns or artists’ deaths.
So What’s In Store For 2025?
Who charting in 2025 will still be on the Hot 100 in 30 years? It’s anyone’s guess. While you’d be wise to never bet against Taylor Swift, a smarter projection would be Mariah Carey and the 37th annual No. 1 return of “All I Want For Christmas Is You.”
And as artists — and non-artists alike — begin to avail themselves more of artificial intelligence while making songs, don’t be surprised if Billboard has softened its stance by then and allows AI-powered songs to grace their charts.
Put it down.
And, in the meantime, have a Happy New Year 2026!
DJRob
DJRob (he/him) is a freelance music blogger from the East Coast who covers R&B, hip-hop, disco, pop, rock and country genres – plus lots of music news and current stuff! You can follow him on Bluesky at @djrobblog.bsky.social, X (formerly Twitter) at @djrobblog, on Facebook or on Meta’s Threads.
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