Reasonable Doubts: Jay-Z’s Biggest Regrets

In recent a interview about his new book Decoded, Jay-Z seemed to express some remorse about lyrics he’d recorded for “Big Pimpin”. Since he doesn’t write his rhymes down seeing them on the page for the first time gave him pause. He told the Wall Street Journal that the words were “harsh” and that “It was like, I can’t believe I said that…What kind of animal would say this sort of thing?”

In 1996 Jay-Z’s “Regrets” stood out as one of the best song on his debut, Reasonable Doubt. As Jay pimp struts into his middle-aged years we imagine he has quite a few more regrets to add to his tally. In light of his “Big Pimpin” revelation and the release of Decoded we’ve made a list of what not-so-young Hov wishes he could take back.
5) “The BluePrint 2”

Easily the most un-focused of his catalog The Blueprint 2 was panned for being the polar opposite of its predecessor. Where The BP was lean and soulful, BP was bloated and pretentious. He even went into the lab attempting to trim the fat and re-released the project as the Blueprtint 2.1 but no on was fooled. Jay-Z wouldn’t touch the Blueprint franchise again until 2009. In hindsight, tagging it “the gift and the curse” might not have been such a good idea.
4) “Super Ugly”

Smarting from the verbal uppercuts of Nas’s “Ether” Jay-Z hurried into the studio and hijacked Nas’ “Got Yourself” and Dr. Dre’s “Bad Intentions” instrumentals (how appropriate) and unleashed a blitzkriege of personal info about Nas, including that he’d slept with his baby’s mother Carmen and left condoms on her baby seat. The diss was perceived by many to be desperate, reactionary and not in the same class as his first shot “Takeover.” Even his mother made Hov get on the radio and apologize for hitting below the belt. Allen Iverson wasn’t happy about being thrown under the bus either, as Jay insinuated that he slept with Carmen as well–and he was married at the time.
3) “Ride…or Die”

In 2005, Jay-Z lost his nephew in a car crash. He was driving a Chrysler 300 given to him by uncle Hov as a graduation present. Jay-Z documented the death on “Lost One” rhyming “My nephew died in the car I bought/so I’m partly under the belief it’s partly my fault.”
2) “Guilty Until Proven…Guilty…”

After debuting the video to “Do It Again” at Irving Plaza Jay-Z and Dame Dash rolled up on Lance “Un” Rivera at listening party for Q-Tip’s Amplified and stabbed the Undeas Exec for allegedly bootlegging In My Lifetime Volume 3. Hov pled guilty to third-degree assault and was sentenced to three years of probation. He was facing 15 years if the case had gone to trial.
1)”Justify My Thug…”

At the age of 12 Jay-Z shot his brother in the shoulder for stealing his jewelry. The way the story is told it sounds like Jay was just a materialistic kid protecting his belongings. However, Jay-Z told Oprah that his brother was “dealing with a lot of demons” and said that his 16 year old brother was stealing things to feed his drug habit. So while Jay may not like talking about it, he’s more like Ossie Davis in Jungle Fever putting Gator Down for stealing than Nino Brown. And contrary to some reports this is not new news and he spoke on the incident in the 1997 song “You Must Love Me.” “Saw the devil in your eyes, high off more than weed, confused, I just closed my young eyes and squeezed…”
While we’re sure Jay has plenty to be thankful for this Holiday, we also know he’d love  to have a  reset button on these.
-EZ Street