Remember “The Three Daves” episode from the 2nd season of The Chappelle Show? If not, in the hilarious episode, Dave acted as himself from three different ages (18, 24, 30) handling different topics (relationship problems, fighting the law, professional rejection).

Unless you have been living under a rock for the past three weeks, there’s another superstar in the news going through another drastic transformation in his career:

Jay-Z.

[ALSO READ: Jay-Z and Beyonce Become Music’s First Billionaire Couple, Reddit Co-Founder Wants Jay-Z’s Nets’ Share]

The Brooklyn lyrical titan has signed a multiyear deal with Universal Music Group for his Roc Nation record label, began a sports agency(then subsequently signed Robinson Cano), was named one of the 100 Most Influential People by TIME Magazine(for the SECOND time) and April is barely halfway over. A lot has changed since Jay was rapping faster than a caffeinated Twista and dressing baggier than Fat Albert.

There are three Jay-Z era’s in his illustrious 14 year recording career (minus his two year retirement).

’96-’00 will be known as his Rise to Stardom/Project Boy Grows Up.

’01-’03 is his Ascenion To Greatness/New Rap King.

’06-present is Icon Hov

So let’s take a look at The Three Jay’s:

Jay-Z on Fashion:

Rise to Stardom/Project Boy Grows Up (’96-’00):

“So I’m cruising with this Bourgeois broad/

She said “jigga man, why don’t you take the du-rag off/

Hit a U-Turn, ma, I’m dropping you back off.”-“So Ghetto” from Vol. 3 Life and Times of S. Carter

Rule No. 1 for Ladies Wanting To Date Jay-Z back then: Durag > you. Jay-Z always personified his mafioso and decadent lyrics with suits that would make Frank Lucas proud during the Reasonable Doubt days. But like he says later in the song, he was still a “thug n*gga ’till the end.”

Ascenion To Greatness/New Rap King.(’01-’03):

“And I dont wear a jersey, I’m thirty plus/

Give me a crisp pair of jeans, n*gga, button ups”-“What More Can I Say” from The Black Album

You want to know how drastically Jay-Z changed between age 30 and age 33? He released The Blueprint album at 30 and The Black Album at 33. On “Jigga That N*gga from The Blueprint he said:

Come on the track duh duh da-da
With a throwback jersey and a fitted

He dropped Mitchell & Ness quicker than he did Amil.

Icon Hov (’06-present):

“Throwbacks, I threw ’em back, remember the button ups”-“Reminder” off of Blueprint 3

I like to call this Rocking Chair Hov. The older he gets the more reflective he becomes of his career. He’s one half of music’s first billionaire couple so he’s super comfortable in dressing in anything now. Even if that means looking like George Costanza:

[ALSO READ: Jay-Z Officially Applies To Be A Baseball Agent]

Jay-Z on Love:

Rise to Stardom/Project Boy Grows Up (’96-’00):

“She wanted, us to end, cause I f*cked her friend/

She gave me one more chance and I f*cked her again/

I seen her tears as she busted in/

I said, “sh*t there’s a draft, shut the door b*tch and come on in!” from “Jigga What, Jigga Who” off Vol. 2 Hard Knock Life

He was brash and unapologetic earlier on before he had political connects to upset. He even “dated” this woman:

Something tells me not many women got past a firs date with younger Young Hov.

Ascenion To Greatness/New Rap King.(’01-’03):

But ma you got a f’real f’serious role
I’m bout to give you all the keys and security codes from “Excuse Me Miss” off The Blueprint 2: The Gift & The Curse

In 1999 Mr. Carter was ending dates if a woman disrespected his durag. In 2001, he said he was going to “mourn forever” for failed relationship on “Song Cry”. By 2002 he was sounding like he was ready to get married with no prenup.

Coincidentally, this line was on the same album he had his first collaboration with his future wife and mother of his first child, Beyonce. The things a woman can do.

Icon Hov (’06-present):

“The most amazing feeling I feel
Words can’t describe what I’m feeling for real
Maybe I paint the sky blue
My greatest creation was you”- from “Glory”

On this one song he tries to hit a high note, says the father who abandoned him was good deep down inside, and even talked about Beyonce’s miscarriage. He even slides in a sly reference to the late Aaliyah(check your carry-on baggage, seriously). He has a wife and and a child. This is what rap at 40 should sound like.

*Cues Blue Ivy’s outro*

[ALSO CHECK OUT: New Music: Jay-Z’s New ‘Open Letter’ Discusses Everything From Obama To Cuba To ‘New World Management’]

Jay-Z on Enemies:

Rise to Stardom/Project Boy Grows Up (’96-’00):

“You’re twitchin, don’t do that, you makin me nervous/

My crew, well, they do pack, them n##### is murderous” from “Friend or Foe” from Reasonable Doubt

On numerous occasions Jay-Z has said when he started rapping he was just doing it to impress his friends.He was coming out of the drug game and relinquishing that mentality was not quick. In 1999 he pleaded guilty for assault after stabbing record producer Lance “Un” Rivera over the latter bootlegging his album.

Ascenion To Greatness/New Rap King.(’01-’03):

“When the grass is cut, the snakes’ll show/

I gotta thank the little homie Nas for that though/

Saving me the hassle of dealing with half of these a*sholes

And I’mma let karma catch up to Jaz-O.”- Blueprint 2″ from Blueprint 2: Gift & The Curse

Simply put: Jay-Z wanted to be the greatest rapper of all time so it is no surprise that on the same album where he says he’s the closest to B.I.G. he aims at all his targets on “Takeover”. From bringing out Michael Jackson at Summer Jam(BEFORE the Prodigy picture) to selling out Madison Square Garden, he was ready to distinguish himself from the others and show he was in a class of his own.

Just don’t listen to “Renegade”.

Icon Hov (’06-present):

“Tell Rush Limbaugh, to get off my b*lls/

It’s 2010, not 1874”- “Off That” from Blueprint 3

This man said that he told the President of the United States of America to quit his job and take a vacation with him on the beach. He’s in rarefied air for a Hip Hop artist. So naturally his enemies turn from angry rappers to angry politicians and political pundits. Let’s just hope he doesn’t start beef with any dictators.

Jay-Z On His Rap Legacy

Rise to Stardom/Project Boy Grows Up(‘ 96-’00):

“I’m from where n*ggas pull your card, and argue all day about
Who’s the best MC’s, Biggie, Jay-Z, and Nas”-from “Where I’m From” from In My Lifetime Vol. 1

At his core, Jay-Z is a competitor. He once battled DMX in a Bronx pool hall in the 90s. He once rapped on radio with Big L for 10 minutes. Not for money but just to showcase his skills. Young Hov always had his eyes on the throne.

Ascenion To Greatness/New Rap King.(’01-’03):

“If I ain’t better than B.I.G. then I’m the closest one”- “Hola Hovito” from The Blueprint 

There was a void in Hip Hop after 2000. Notorious B.I.G., Tupac, Big L and Big Pun had died within the last 4 years. While Nas was yelling there is no Best Rapper of All Time, Jay-Z was cornering the market and letting the new generation of Hip Hop know early who the G.O.A.T. was.

Icon Hov (’06-present):

“Hov got flow though he’s no Big and Pac, but he’s close
How I’m ‘posed to win? They got me fighting ghosts” from “Most Kingz”

Jay-Z is considered by a large consensus to be the Greatest Rapper of All Time but the ghosts of Tupac and Biggie still linger. He is no longer competing with anyone but simply carving himself into Hip Hop’s Mount Rushmore next to them. ‘

A sports agent. A former part NBA owner. A husband in a billion dollar relationship. He is done trying to say he’s the best, he’s just redefining what that “best” means.

[ALSO READ: Jay-Z Covers TIME Magazine’s 100 Influential People, NYC Mayor Michael Bloomberg Writes The Article]