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Lil Wayne is one of hip-hop’s most iconic characters. He’s also come through with some truly crazy rap lines over the years.

His career dates all the way back to age 12, when he debuted as ‘Baby D’ on the collaborative album True Story in 1995. His first solo album was Tha Block is Hot, which dropped in 1999, when Wayne was just 17 years old.

Since the late ’90s Wayne has contributed to the culture in countless ways. For many, he’s the king of southern rap. Hailing from New Orleans, Louisiana, Tunechi brings lyricism to the South in ways not many had done before him.

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Part of what makes Lil Wayne unique is the manner in which he constructs his rhymes. A master of metaphors and double entendres (a way to have one line have two different interpretations), he’s often overlooked as a rap goat because of his penchant for seemingly simple raps about drugs and oversexualizing women.

At age 39, Weezy F. Baby doesn’t appear to be slowing down anytime soon. In the last few years he’s released multiple albums and mixtapes, and apparently has more new work on the way.

With all that said, let’s take a look at some of Lil Wayne’s wackiest – and most brilliant – raps to date!

1. ‘Steady Mobbin’ – We Are Young Money (Album)

‘Big House, long hallways – Got 10 bathrooms, I can sh*t all day’

Tune didn’t hold back from stunting his ass off, literally, on this classic from 2009.

2. ‘Lollipop’ Remix – Tha Carter III (Album)

‘Safe sex is great sex, better wear a latex – Cuz you don’t want that late text – that “I think I’m late” text’

Weezy takes his sex-ed seriously. Very seriously. 

3. ‘Blue C-Note’ – Collegrove (Album)

‘I keep on switching wifeys, you gotta Uncle Phil (feel) me’

Playing on the Aunt Viv drama from the 90’s classic sitcom The Fresh Prince of Bel-Air, Wayne eludes to how he’s likely not to settle on a main wife anytime soon.

4. ‘This Is The Carter’ – The Cartar (Album)

‘You watch ya grill what ya oughta do, before ya ribs get barbecued’

On his inaugural album to The Cartar series, Tune held no punches on the title track.

5. ‘Upgrade U Freestyle’ – Da Drought 3 (Mixtape)

‘Peel off in a Lamborgin, like a tangerine – Got the industry straight shaken like a tambourine – Like a b*tch with some lips like Angeline’

Wayne let loose all over Da Drought 3, a mixtape that many believe is his best body of work to date.

6. ‘BM Jr’ – Tha Carter

‘And when we hungry, you look like pie – Sweet potato ass n*gga, you lemon meringue, apple custard, cherry jelly – Don’t make me get the biscuit buster’

Back to the tape that made Lil Wayne the Lil Wayne we know today, Tunechi gets crazy on this track that pays homage to his former mentor Birdman. He must really like his sweets.

7. ‘Swag Surg’ – No Ceilings (Mixtape)

‘Quarterback, shotgun, you don’t get any sack yards – B*tch I ball hard, breaking all the backboards – Pretty Boy Floyd, step up I will smack yours – And even at the White House I pull up at the back door’

Sheesh. In a matter of seconds, Wayne drops crazy metaphors, a couple of double entendres, shouts out Floyd Mayweather, and stunts on everyone listening by saying he has access to the back door of the White House. I don’t believe him about that last part, but they’re still fire bars.

8. ‘Seeing Green’ – Beam Me Up Scotty (Mixtape/Nicki Minaj)

‘But I’m the greediest shark amongst a ocean of killers – I’ll put you six feet deep, I’m being socially distant’

Lil Wayne and Drake linked with Nicki Minaj to reprise her iconic third mixtape ‘Beam Me Up Scotty’. 

9. ‘Used To’ – If You’re Reading This It’s Too Late (Album/Drake)

‘Tell her that I love her and I hate her in the same sentence, I’m f*cking her mind’

Drake has been a prime collab partner for Lil Wayne for over a decade. This simple bar provides depth to a common thought possessed by most rappers.

10. ‘Racks’ – Sorry 4 The Wait (Mixtape)

‘Real n*gga since day one, cause I ain’t promised day 2 – Throw that p*ssy at me, b*tch I think I’m Babe Ruth’

For those that don’t know, Babe Ruth is an old-school baseball player who hit a lot of home runs.

11. ‘Bandz a Make Her Dance (Remix)’ – Single (Juicy J featuring Lil Wayne and 2 Chainz)

‘What’s yo real name? And not yo stripper name – I’ll make it rain on ya, like a window pane’

Weezy is certainly underappreciated for his ability to spit dope metaphors… even if they are only about one or two different things.

12. ‘No Love’ – Recovery (Album/Eminem)

‘Money outweighing problems on a triple-beam – I’m sticking to the script, you n*ggas skipping scenes’

Wayne hooked up with Eminem on this 2010 project. Weezy brought the slow flow on this record, which perfectly contrasts with the quick rhyme-scheme from Eminem.

13. ‘6 Foot 7 Foot’ – Tha Carter IV (Album)

‘I lost my mind, it’s somewhere out there stranded – I think you stand under me, if you don’t understand me – Had my heart broken by this woman named Tammy – But hoes gon’ be hoes, so I couldn’t blame Tammy’

I’m usually not a fan of the same word being used in back-to-back lines, but somehow this time it just seemed like the right thing to do.

14. ‘Phone Home’ – Tha Carter II (Album)

‘I can get your brains for a bargain, like I bought it at Target – Hip-Hop is my supermarket, shopping cart full fake hip-hop artists’

The Carter series has been good to Lil Wayne, and this alien-esque track is filled with out-of-this-world lyrics.

15. ‘Sh!t’ – Sorry 4 The Wait 2 (Mixtape)

‘I smirk when I squeeze, trigger smart, street smart, I’m a nerd, I’m a geek – I’m absurd, I’m unique – Spent my time at Cash Money, time served and released – But this agent ain’t free, that’s the word on the streets – But that sh*t is old news, that sh*t so yesterweek’

I’m a big fan of Mixtape Wayne. Clearly.