Music Monday: Nelly

Each Music Monday will be formatted as followed: an overview/ my opinion on their said career, followed by the ranking of their top 5 songs. No artist is without flaws, their worst three songs will also be judged and ripped to shreds.

As a reminder, this is not going to be a series where I list no-name songs off an artist’s shitty second album that’ll you’ll hear occasionally in an urban coffee shop. We only grade hits here. I’m not looking for songs that have the best underlying message. I’m not looking for songs that represent the artist’s struggle and triumph over something shitty that happened to them. I don’t care about any of that. We are only ranking the cream of the crop, the pinnacle of an artist’s success. Before you ask, I will not be ranking The Beatles’ songs, as I do not want to tarnish my blog with overrated garbage. If you have a problem with that, or my rankings, and want to make your criticisms known, you can email all of your concerns to VinnieWontCheckThis@gmail.com. Prior versions of this series can be found here.

So with that, let’s get started.


Cornell Iral Haynes, Jr was born on November 2, 1974 in Austin, Texas. When he was a teenager, he moved with his mother to St. Louis after his parents divorced. While in high school, Nelly formed the rap group St. Lunatics with his friends Ali, Murphy Lee, and his half brother City Spud. Despite being popular in Missouri and the surrounding areas, the group struggled to achieve success outside of St. Louis. The rest of the group agreed to let Nelly go solo after a major record deal failed to appear. Nelly was unusual for being a rapper from the Midwest at a time when hip-hop was dominated by the East Coast, West Coast and the South. The label used this to their advantage by branding Nelly as a star of the Midwest, hoping to inspire pride in the people of St Louis and the surrounding regions. He released his debut album, Country Grammar, in 2000. The album spawned a top three hit (Ride Wit Me), top ten hit (Country Grammar), and a top 15 hit (E.I.). The album was a commercial and critical success, becoming the 9th hip hop album to ever be certified Diamond, selling over 10 million copies. The success of the album lead to him performing at the halftime show of Super Bowl XXXV alongside N’Sync, Aerosmith, Britney Spears, and Mary J. Blige. He followed Country Grammar up with Nellyville in 2002. Nellyville became the 14th best selling rap album of all time. It spawned two number hits (Hot in Heree, Dilemma), and a top three song (Air Force Ones). He won three Grammy’s including Record of the Year, Album of the Year, and Best Collaboration. His 2003 hit, Shake Ya Tailfeather, which was apart of the Bad Boys II Soundtrack, gave Nelly his third number one song. It also won a Grammy for Best Collaboration. He performed for the second time at the halftime show of the Super Bowl, performing at Super Bowl XXXVIII, appearing right before Janet Jackson’s top fell out. In September 2004, he released a double album Sweat/Suit. Both albums debuted number one and number two upon their release, selling 5 million copies. Two songs from the Suit side of the album hit number three and number four on the charts, respectfully. (Over and Over, My Place). A year later he released a deluxe edition of Sweat and Suit, titled Sweatsuit, which consisted of the same songs off the double album, as well as three new tracks, one of which hit number one on the charts (Grillz). Over the next couple of years he tried his hand in acting before releasing Brass Knuckles in August 2008. The album didn’t have any songs chart in the top 20. His fifth album, 5.0 was released in November 2010. It spawned a top three hit (Just a Dream), which became his best selling song since Grillz. In 2013 he appeared on the remix to the Florida Georgia Line song Cruise which hit number five on the charts. He rode the success of this song into another album, M.O., released in September 2013, as well as a reality show which ran for two seasons. 2015 began a three year stretch of numerous Dilemmas where Nelly found himself getting arrested Over and Over again. It all started in 2015 when he was arrested for meth and gun possession. He followed this up in 2016 when he was arrested for tax evasion, owing more than $2.4 million to the IRS. Lastly, in 2017 he was arrested after being accused of rape. Good gracious them charges bodacious.


Nelly is is an icon. Just a cool as hell dude. He was Drake before the world wanted a Drake. He wore a band-aid as an accessory. He was able to talk to girls using Microsoft Office software. You can argue he was a top three rapper throughout the 2000s. Him releasing Country Grammar and Nellyville back to back was music equivalent of Kobe and Shaq both average 31 a game during the 2001 playoffs. He had the second most top 10 hits by a hip hop artist in the 2000s. Despite all of this, it feels like he doesn’t get nearly as much praise as he should. That changes right now. Let’s grade Nelly’s hits.

5. Shake Ya Tailfeather (ft. Murphy Lee & Diddy): I absolutely adore this song; my mother on the hand hates it. Namely, she hates the intro with the police sirens. Her and I were driving one time and this song came on the radio and mother, being the good Samaritan that she is, actually pulled the car over on the highway once those sirens started blaring. Once she realized what she had done, she was out on this song. Not even Murphy Lee’s brilliant verse could have convinced her that this song is in fact very good, which is a modern tragedy.

4. Dilemma (with Kelly Rowland): Here is a fun fact about the song. In the music video, Kelly Rowland tries texting Nelly through Microsoft Excel. One time I tried texting a girl I wanted to come over, and much like Kelly, I had the wrong cell. The problem was, this girl was probably in some other guy’s sheets. That pretty much =sum()’s up my love life.

3. Country Grammar: How good is this song? Nelly had us signing a chorus about drive-by shootings with the most positive energy imaginable. What a tune.

2. Grillz (ft. Paul Wall): Ah who can forget the song that made every middle schooler put the 5-Gun wrapper around their teeth. There is a very short list of songs that will never receive the skip button. This is one of them.

1. Ride Wit Me: this song is an instant mood changer. I think the closest that this society ever got to world peace is when this song came out.


Everybody says that Lil’ Naz X brought Country-Rap to mainstream music, whilst overlooking some of the cross genre work Nelly has done. Since country has been a big part of Nelly’s career, it’s time we rank the best Country songs Nelly’s ever done.

4. Die A Happy Man (Thomas Rhett Cover): yes this is real and it isn’t terrible. Nelly is secretly a country boy at heart.

3. Over and Over (with Tim McGraw): the day this song was released was the one time in US history that racism didn’t exist.

2. Country Grammar: see what I did there?

1. Cruise Remix (with Florida Georgia Line): Billy Rey Cyrus and Lil Naz X could never make a classic like this


Your Turn

If you had a blog and were to rank every Nelly song that hit top 20 on the charts, what are your top 5?

TitleYearPeak chart positionsAlbum
Country Grammar (Hot Shit)20007Country Grammar
E.I.200015Country Grammar
Ride wit Me (ft. City Spud)20013Country Grammar
Hot in Herre20021Nellyville
Dilemma (ft. Kelly Rowland)20021Nellyville
Air Force Ones (ft. Murphy Lee and Ali)20033Nellyville
Shake Ya Tailfeather (ft. P. Diddy & Murphy Lee)20031Bad Boys II Soundtrack
My Place (ft. Jaheim)20044Suit
Over & Over (ft. Tim McGraw)20043Suit
Grillz (ft. Paul Wall & Ali)20051Sweatsuit
Just a Dream201035.0

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