Entertainment
How Jay-Z Changed Rap With ‘Reasonable Doubt’

If you went back in time to New York in the early ’90s, not a soul would believe you if you told them Jay-Z would end up where he is today. Well, maybe one person would: Jay himself.
Jay-Z’s relatively delayed breakthrough made him something of a late bloomer, even in an era when stars weren’t minted as quickly and early as they are now. It took him a while to figure out how to be himself on wax. It was his big homie Jaz-O who put him on, and the two of them had a Das EFX, Fu-Schnickens fast-rapping style that was as technically impressive as it was uninteresting. The labels didn’t know what to do with them. Those who heard them tended to think Jaz was cool, but that the light-skinned kid had something else they couldn’t quite put into words.
DJ Clark Kent was Jay’s biggest cheerleader at that time, but without label interest, Jay figured he was better off prioritizing his life in the streets over the studio. Things continued that way until Clark introduced Jay to Harlem hustler Dame Dash. The pair clicked, and together with another street guy, Kareem “Biggs” Burke, they decided to pool their resources and start their own label, Roc-A-Fella. Their first project would be Jay-Z’s proper debut, Reasonable Doubt, which turned 30 this week.
On Reasonable Doubt, the fast, wiggety-spiggety rapper from “Hawaiian Sophie” is gone. Instead it’s the Jay we’re a lot more familiar with: not just the hustler, but the boss. Selling pounds instead of nickel bags. Rapping about the expensive cars, champagne, and a lifestyle viewed from a vantage point higher than what you typically found in street rap of the time. He gave you ambiance while others just rhymed.
Aside from the rapping itself, a big part of why Reasonable Doubt resonates so much still is that it was what we would call today an exercise in personal branding. The success of Reasonable Doubt validated Roc-A-Fella’s early marketing strategy, which included showing up to clubs, shows, and radio stations in fly cars, buying out bottles of champagne, throwing around money very conspicuously. Jay was cool and flashy, but in an effortless way. Dame was flashy and loud, full of that classic Harlem bravado. The glamorous displays helped both advertise the music and authenticate it, proving that everything Jay rapped about had to be true, because you could see evidence of it right before your eyes.
Jay was one of my first “favorite rappers.” He was the coolest guy in the world to me; no one wore a fitted and a big leather jacket better. He was the best at clever turns of phrase, and double or even triple entendres. And as DJ Clark Kent liked to point out, he was the best at saying his rhymes. With his self-assured smirk, he could make anything sound smooth.
That’s what Reasonable Doubt represents to me, even now. Jay-Z differentiated himself by taking the Nas route of using his slick wordplay to tell the tales of the streets. If Nas’s perspective was that of a young man watching the scenes from his project window, then Jay’s was that of a boss in the thick of it, surveilling his domain from inside an Acura Legend parked on the corner. His first verse on “Dead Presidents II” is still as potent as it was 30 years ago: “Can’t stop I, from drinking Mai-Tais, with Ty-Ty/Down in Nevada, haha, Poppa, word life/I dabbled in crazy weight/Without rap, I was crazy straight/Partner, I’m still spending money from ’88.”
His “Bring It On” verse might be my favorite on the whole album: “Mannerisms of a young Bobby De Niro/Spent Spanish wisdoms, in a whip with dinero.” And “Can I Live” speaks for itself: “For precipitation we stack chips, hardly/The youth I used to be, soon to see a million/No more Big Willie, my game has grown, prefer you call me William.”
Reasonable Doubt also serves as a valuable snapshot of a golden age of New York hip hop, a real who’s who of that period: features from The Notorious B.I.G., Foxy Brown, and Mary J. Blige; prominent samples of Nas, Prodigy, and Fat Joe records; beats from some of the most prominent New York producers of the day. Again, there’s that synergy: The collaborations made for great music, and at the same time smart branding, marking him as a peer of rap’s elite on just his first album.
The popular history reads that, after Biggie’s death in 1997, Jay-Z comfortably stepped into those shoes as the new king of New York. However, it’s interesting to remember that at no point in his career was Jay the highest-selling rapper from the city. Instead, his claim to the throne was based on his consistency. For over a decade, you could depend on Jay putting out a new album, and the album would be good. It helped that Jay was always a trendsetter. Any brand, drink, or style he shouted out in a song or flaunted in a video became the hot new thing. Jay was also wise enough to recognize the sleeping giant that was Southern rap. He was a huge fan of Cash Money Records, Scarface, and UGK, and did his part to help normalize them with the often provincial East Coast audience. (At times, he maybe went too far in that direction; the less said about his verse on the “Ha” remix, the better.) From down South, we often looked at his regional crossover efforts as him trying to jump on the wave right as the South was starting to take over. With Jay, both things are usually true. A Jay verse was always an event, whether it was a radio freestyle or a verse on a Mya record. At least until Kanye, it’s fair to say Jay-Z was the most influential rap artist around.
These days, it’s hard to remember that Jay-Z. In 2026, he might as well be Jeff Bezos; he’s as corporate as they come. He’s a guy the NFL could recruit when Colin Kaepernick and anthem kneeling was giving the league too much negative publicity. His last album should’ve come with a CPA exam. He was recently sued for sexual assault, though the accuser eventually dropped the case against him.
Jay is controversial, to say the least, even before getting into his effect within the music itself. He played a key role in rap’s transition from music about the poor and downtrodden to music about “bosses” and “kingpins,” and the rise of luxury lifestyle rap. He’s basically responsible for rappers not physically writing their rhymes anymore, thanks to the lore surrounding his own creative process, which takes place all inside his head. There’s the messy breakup of Roc-A-Fella, which Jay seems to have instigated so that he could leave to become president of Def Jam.
But even now, Jay-Z can have moments where he rekindles that old spark, like at the recent Roots Picnic. It’s been interesting and maybe even a little suspicious to see Jay suddenly leaning hard into Roc-A-Fella nostalgia. Usually that kind of thing is limited, a bone thrown to the fans on every pivotal anniversary. A concert, maybe, or a re-release. This year, Jay seems to be playing it up. There are the shows at Yankee Stadium for Reasonable Doubt and The Blueprint, and the Roc reunion at the Roots’ festival in Philly. Jay brought out Beanie Sigel, Freeway, Peedi Crakk, the Young Gunz, and Memphis Bleek for a big Roc-A-Fella lovefest. He also delivered a freestyle that, if nothing else, proved he still has the ability to make the world stop and take notice.
Jay’s spent a decade content to let everyone reminisce about the good old Roc-A-Fella days, and to gossip about how those days fell apart, and whether or not he sold out his friends to get ahead. Perhaps he feels the need to remind people what they loved about him, given that he’s now most closely associated with being a member of the loathsome billionaire class and helping the NFL whitewash its image. Maybe he understands that this is what sells now. You’d rarely be wrong by reading cynical intentions into anything Jay-Z does.
Entertainment
Trump’s Freedom 250 cancels Vanilla Ice concert two hours before showtime
President Donald Trump’s Freedom 250 has canceled a concert performance by “Ice Ice Baby” rapper Vanilla Ice two hours before he was set to take the stage.
Freedom 250, the president’s public-private organization tasked with throwing celebrations for the 250th anniversary of American independence, announced after 5 p.m. ET Friday that “due to inclement weather” the “Great American State Fair,” where Vanilla Ice was set to perform, will be closed for the rest of the day.
“The safety of our guests, staff, and partners remains our top priority. We are actively monitoring conditions and will provide updates as they become available,” Freedom 250 wrote on X. The organization added that the fair will reopen Saturday at 10 a.m.
Vanilla Ice, whose real name is Rob Van Winkle, called the event a “once in a lifetime opportunity” in an Instagram post hours earlier.
“We’re about to have a great party tonight,” the rapper said in a video on the National Mall, where he was set to perform on a massive stage. “This is gonna be epic.”
In the caption, he wrote: “Once in a lifetime, happy birthday America. Put your dance shoes on. We’re all gonna come together and be teenagers for the night.”
It’s unclear whether the concert will be rescheduled. The Independent has requested comment from Freedom 250 organizers.
Virtually every artist who was scheduled to perform for at the concert series — including Martini McBride, The Commodores and Bret Michaels — dropped out of Freedom 250’s lineup shortly after it was announced.
Vanilla Ice was the last artist standing for Friday’s still-scheduled “I Love the ’90s” concert, which originally featured Milli Vanilli, Young MC and C+C Music Factory.
Young MC dropped out shortly after the lineup was announced, saying the artists “were never told about any political involvement with the event” when they were booked. The musicians behind the lip-syncing duo Milli Vanilli said they never agreed to perform, and Freedom Williams, a rapper who owns the rights to use the C+C Music Factory name, said in a video defending his appearance that he “doesn’t f*** with Trump” before he also apparently backed out.
Vanilla Ice told TMZ last month that he’s “not gonna get dragged” into politics.
“I’m here to party with America, man,” he said. “Music is made to bring people together, and that’s what we are here to do. And we’re just gonna represent the ’90s.”
Once performers started pulling out, Trump stepped in, calling himself the “Number One Attraction anywhere in the World.”
“I am thinking about bringing the Number One Attraction anywhere in the World, the man who gets much larger audiences than Elvis in his prime, and he does so without a guitar, the man who loves our Country more than anyone else, and the man who some say is the Greatest President in History,” Trump said about himself in a Truth Social post last month.
Trump gave a political, rally-style speech to kick off the “Great American State Fair” Wednesday night.
During the speech, the president raved about his renovation projects around Washington, D.C., including his massive and costly ballroom, which is at the center of a legal battle after he demolished the East Wing to make way for the project. Trump also re-painted the Lincoln Memorial Reflecting Pool that turned green from algae days after being completed while freshly applied blue sealant appears to be cracking off.
“For many years, our country was ruled by politicians who let America and its capital fall into decline and total disrepair. The city named in honor of General George Washington was turned into a national disgrace, but not anymore,” Trump told a crowd of supporters Wednesday.
The kick-off event also featured music from Lee Greenwood, who sang his famed song “God Bless the USA,” and FBI Director Kash Patel’s girlfriend, Alexis Wilkins, sang the national anthem.
Wilkins’ performance was blasted online, with one X user posting, “You can hear a better rendition at any high school ball game.”
The cancelations aren’t only hiccups at Freedom 250 since the fair opened this week.
Entertainment
Jeff Schaffer on Obama’s Notes, Curb in History
When “Curb Your Enthusiasm” wrapped up its 24-year-run in 2024, fans were concerned it would be the last time they’d see Larry David on screen. He had been saying the HBO sitcom was ending for the better part of the series’ run, and with Season 12 he finally called it quits. (“I said it before,” he told Variety at the time. “But I wasn’t 76 when I said it.”)
But his longtime collaborator Jeff Schaffer — who, in his early 20s, joined “Seinfeld” as a writer before becoming a major force behind the scenes of “Curb” — always knew David would be back on TV.
“I guess we’re like a plague of locusts, but you don’t have to wait 17 years,” he says over Zoom ahead of the premiere of “Life, Larry and the Pursuit of Unhappiness,” a historical sketch comedy show that he describes as “‘Curb’ in costume.” (Schaffer co-created the project with David and directed all seven episodes.)
The series, which premiered on HBO on June 26, is executive produced by Barack Obama, who also appears in a sketch. In typical David fashion, the “Curb” star plays selfish, petty and unfiltered men throughout history. For every Founding Father looking to free the colonies from British tyranny, there was a Larry (often called Lawrence here) who suggests that sharing desserts and umbrellas should be prohibited by the Declaration of Independence. And in this version of history, Larry takes a stand for Rosa Parks when a white bus driver demands she give up her seat — not because Larry cares about civil rights, but because he’s sitting in the aisle and doesn’t want to get up.
In other words, the show is a celebration of America’s 250th birthday, but one that smears a little cake on the country’s face.
I didn’t think I’d see another project from you and Larry so soon after “Curb.”
“Curb” ended, and we were batting around some ideas. Then this sort of appeared. Larry will forego any opportunity to do things that are offered to him. He’s the great foregoer. But he was interested in this one, and we just started writing.
When you say this idea just “appeared,” it came from the Obamas, right?
Ethan Lewis at Higher Ground reached out on behalf of the Obamas. They wanted to do something for the 250th, and Larry, who is an American history buff, was interested in the idea of Larry going through history. To be honest, the seeds of this started a few years earlier when we did this commercial for FTX — lovely people, I don’t know what happened to them. Basically, Larry went through world history, dumping on every great invention. He remembered how much he liked being in costume, and he forgot how much he hated being in wigs.
So, Larry took a shine to this idea very quickly, in a way that Larry rarely takes a shine to anything. It helps that he and President Obama have a really good rapport, as you see in the show. From the first meeting, it was like, “We’ve got to get these two on screen together.”
When “Curb” ended, there was a concern among fans that Larry might be done with making television. You never shared that concern.
Larry can’t sit still. He’s like a prostitute who has sex when he’s not working. He’s always writing and thinking about stuff. We were actually in the beginning stages of thinking about other things to do after “Curb.” There was a movie we were thinking about, and there was a possible limited series we were thinking about, but this seemed appealing for a variety of reasons. One was working with the Obamas, and two was that the show had a deadline. It had to be done by now for the 250th.
The idea that it was eventized appealed to us. We said we’d do six episodes, and that’ll be that. It didn’t feel like it had the full weight of a series where you have to worry about Season 2 or Season 3. It was just a lark. But we ended up making so many sketches that we did seven episodes. Frankly, the thing that really appealed to Larry is that he loves American history. He studies it. This is a man who has the Gettysburg Address in his bathroom.
Does he really?
Yeah, his office bathroom has the Gettysburg Address. That’s where we got that “Curb” bit from. He doesn’t want to waste his urination time. Like his urination, those fallen soldiers of Gettysburg shall not be in vain.
“Life, Larry…” has a very “Curb” sensibility. Were those other ideas you and Larry considered — the movie and the limited series — similar?
We never stray far from the “Curb” sensibility. Larry still has ideas. I always say, “Until you can walk outside and not be annoyed by your fellow man, we’ll have a job.” So the question is, “What kind of vessel do you pour those ideas into?” Is it a movie that has fun “Curb” ideas? A limited series or a historical sketch comedy?
Since “Seinfeld,” Larry’s comedy has always been “big thing, little thing.” It’s like, “Hey, we’re going to get to make our own pilot. Wait, who stole the raisins?” There’s always this juxtaposition of a big thing you should be caring about and the little thing that’s somehow dominating your attention. When you get into these historical events everybody knows, the big thing is already right there in front of you. So we can just have fun with the little thing, and that juxtaposition really tickled Larry.
To what extent is this show scripted, compared to the outline structure of “Curb”?
The writing process and the shooting process were very similar to “Curb.” There wasn’t a full script, there was an outline. We probably had a few more lines in it for historical stuff, but it’s still an outline. And then we got fun people to come and play with Larry. Everybody came in for a day — the only person there for two days was Kathryn Hahn, just because of locations. So you have your outline, and every scene is a live rewrite, same as “Curb.” The thing that was different was the way we shot it. This is much more cinematic than “Curb.” Larry didn’t want them to feel like sketches; he wanted them to feel like shorts or little movies. We’re on location — we built the World War I trench and the Wright Flyer. Our production team and costume team took great pains to make it look as real as possible, and then we just drop Larry in and watch all hell break loose.
Were there certain castings that clicked immediately when you were brainstorming?
We started by writing down a list of big events and small events and going, “Which one do we have an angle for today?” One of the first obvious things was that Larry is the guy who told Lincoln to go see that play. We knew that arc right from the beginning, and Larry was like, “Kathryn Hahn needs to play Mary Todd Lincoln, and boy, it’d be funny if Bill Hader was Lincoln.” When we started writing the Lewis and Clark thing, that was about a boys weekend. It had a “Honeymooners” feel to it, and we thought, “Let’s get Larry and Jerry in a ’50s sitcom tone.”
Were there any historical events you explored but ultimately couldn’t find an angle for?
We played with Yalta for a while. We had a Gold Rush sketch that we wrote and rewrote, and we couldn’t figure out the ending. We put in a new ending and — well, it’s not in the show. It had funny parts, but it didn’t have a good enough angle.
While making the show, did you learn anything about history that surprised you?
There were a whole bunch of things. Larry goes, “We should do a popular vote thing with Samuel J. Tilden.” I’m like, “Samuel J. who?” Sometimes doing the research gave us our way in. Everyone thinks Thomas Jefferson wrote the Declaration of Independence, but there was actually a committee of five, with Jefferson and Adams and Franklin and Roger Sherman and Robert Livingston. Actually all of them took the first crack at it, so that was our angle. Larry is Robert Livingston, and this is his first draft. Our main thing was that Larry was rarely listened to, and that’s a good thing for history because when he was, it was met with terrible results.
A funny thing the show illuminates is the idea that people throughout history — even people involved in these world-changing events — were probably talking about really dumb shit and airing petty grievances.
As long as there have been people, there have been petty complaints about people. It’s not like talking shit started in the 20th century.
I’m curious about Obama’s role in producing the show. Did he ever use his executive power? No one is going to say no to the president if he asks for a certain guest star or more budget.
Using a presidential veto to get more money would have been amazing. I wish I’d thought of that. “The president needs an extra three days of shooting. He demands it.” We should have done that.
But the president’s input — and [Higher Ground’s] Ethan Lewis and Joe Paulsen’s — was invaluable. From our first meeting, he had read a whole bunch of stuff and was really liking it. He gave a few notes about something and Larry went, “Yeah, yeah, yeah, we got it.” And the president goes, “I spent a half an hour talking about how funny everything is. I give you one note and you get into a defensive crouch.” The president said, “When I was in the Oval Office, I took advice and listened to my advisors, and I was the president of the United States.” And Larry just goes, “Yeah, but I’m the president of this.”
As you said, this show is billed as a limited series. But, if given the chance, would you want to do more of it?
We had a blast. I mean, with Larry, you’re talking about the guy who said every season of “Curb” was the last season. There is nothing he relishes more than being done with something, but he also never stops working. It’s one of the delightful paradoxes of Larry: can’t wait to finish, always starting something. I don’t know if enough time has passed where he’s forgotten how much he hated being in wigs, but we’ll see. We’re going to do something. There’s a lot more history left on the table, that’s for sure.
So the two of you are definitely not hanging up the hat after this?
No, no. Like I said, people are still irritating.
This interview has been edited and condensed.
Entertainment
MFT breaks up after the Tongans walk out on Solo Sikoa
Last week on SmackDown, MFT members Tama and Talla Tonga asked Solo Sikoa to stay in the back when they challenged Damian Priest and R-Truth for the WWE tag team championship. They didn’t want Solo’s obsession with Jacob Fatu and Roman Reigns to potentially mess with their business in the ring.
Solo eventually showed up at ringside anyway, of course, and MFT ended up losing. Sikoa then took it upon himself to crash this week’s episode of Raw and help LA Knight beat Jimmy Uso.
It turns out that was the last straw. On tonight’s (June 26) episode of SmackDown, the Tongans told Solo they are sick of getting dragged into his war against Roman. They heard from the elders of the tribe, and they’re done with him.
Sikoa was incredulous upon hearing this unexpected news, loudly shouting out that nobody leaves him.
Do you think Tama and Talla Tonga are now heading over to join Roman’s reunited Bloodline after hearing from the elders and abandoning Sikoa? Let me know in the comments below, Cagesiders.
Catch up on all the results from SmackDown in our live blog right here.
Entertainment
Appeals Court Orders Harvey Weinstein Resentencing, Though Conviction Stands
A state appeals court has upheld Harvey Weinstein’s rape conviction in California while ordering him to be resentenced.
Weinstein is currently serving a 16-year sentence for his California conviction, the higher end of the maximum term because of his prior guilty verdict in New York. A three-judge panel of California’s 2nd District Court of Appeal found on Friday that the sentence should be revisited after that conviction was overturned.
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“The sentence is vacated and the matter is remanded for resentencing,” noted the docket. “In all other respects, the judgment is affirmed.”
In a statement, a spokesperson for Weinstein said the former film producer will appeal to the California Supreme Court and that his lawyers “remain confident that significant legal issues deserve further consideration.” He added, “While the court affirmed the convictions, it also recognized that Mr. Weinstein is entitled to a new sentencing hearing.”
The order was issued the same day that a New York state court judge dismissed a third-degree rape charge against Weinstein after Manhattan prosecutors said they wouldn’t pursue a fourth trial. He awaits sentencing for a conviction on a single court of criminal sexual act against former Project Runway assistant Miriam Haley. Prosecutors said they’ll move for a 20-year prison term.
Since 2020, Weinstein has faced four trials in two states. Two juries in New York have deadlocked on a charge related to whether he raped Jessica Mann, who elected not to proceed testifying in a fourth trial, in a hotel room in 2013.
“It is clear, when a convicted rapist is awarded privileges to continue to shield a jury from past settlements, nondisclosure agreements, prior convictions, or other abuse, there is no true justice for a victim of sexual assault when that rapist is a predator,” she said in a statement.
In 2024, the New York’s highest court overturned Weinstein’s 2020 rape conviction after finding that the judge who oversaw the trial “erroneously admitted testimony of uncharged, alleged prior sexual acts” in what amounted to an “abuse of judicial discretion.”
Unlike in New York, courts in California are allowed to introduce evidence that demonstrate a defendant’s propensity to commit sex crimes, even when the allegations haven’t led to formal charges. Such evidence is only allowed in New York courts when it’s necessary to provide history on a defendant’s motive, intent or common scheme to carry out the alleged crimes.
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Jey Uso: ‘I really don’t care about the fans no more’
”I really don’t care about the fans no more. Because when I was doing my thing, they saw the hate. I can’t miss it. It’s all in my face. Social media, whatever it is, when my name pops up, I see it out there…most dislikes video on WWE’s social media platform. Look it up uce, like five, six, ten videos out there.
It’s all good. If anything…that thing lit a fire under me. All the noise, all the opinions. Cool. It is what it is, ‘cause that’s part of the job.”
“I take it back. It’s 50/50, man. Like I said, I’m confused. Pulling me left and right. I yeet. I talk crap…my day ones know who they are. But there [were] a lot of people who did doubt me. Still doubting me right now.”
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