10. 5 O’clock
5 O’clock is off of the 2007 album rEVOLVEr, my least favorite T-Pain album of all T-Pain time. However, it takes a special prowess to take one of Lily Allen’s sappiest songs and turn into an R&B jam. The lyrics are little much at some points, and I could do without Wiz Khalifa’s verse entirely, but this song is essential T-Pain.
9. Can’t Believe It (ft. Lil Wayne)
Fun fact: there’s a remix of this song featuring Justin Timberlake and the artist formerly known as Bow Wow. Don’t listen to that version though, it's trash. "Can’t Believe It" is the perfect display of T-Pain’s nice guy tendencies. In the same four minute span that Lil Wayne talks about showing his potential mate “what these tear drops ‘bout”, Pain tells his girl he’s letting her choose between a condo in Toronto or a mansion in Wisconsin (Wiscancin if ya nasty). If that’s not the definition of hood love, then I don’t know what is.
8. Freeze (ft. Chris Brown)
This song makes the list not simply because it's a great T-Pain song, but mainly because it's one of the final appearances of the Chris Brown we wish we still had. I’m 95% sure Chris Brown left the filming of his The OC story arc to record this song. The music video is also a Skullcandy colored trip that requires exactly one viewing. No more.
7. Booty Wurk
The song literally gives you instructions on which order you need to move your butt cheeks when you’re dancing. What more is there to say?
6. Up Down (Do This All Day) [ft. B.o.B]
Up Down is a pregame staple in my book. The chorus is setup in this call and response structure that allows you and your crew to vibe with each other over that third round of 21 y’all are playing. It's also the T-Pain certified “strip club anthem”, so you should put a single dollar bill in the air out of respect when you hear it.
5. Take Your Shirt Off
What Animal House did for PWI’s, the Take Your Shirt Off video did for southern HBCU culture. The video is the most genuine ode to Tallahassee that exists on this Earth, and as an alum of Florida A&M University gives me Trump levels of pride. I’m surprised The Moon (the Tally club that the video was shot in) didn’t start charging an extra cover for this cameo because its basically the hood version of 1OAK now.
4. Good Life (ft. T-Pain)
Yes, Good Life is technically a Kanye West song, but it is so critical to mention when talking about the T-Pain cannon of music for a few reasons. First, it won T-Pain his first Grammy for Best Rap Song of the Year. Crank Dat by Soulja Boy was also nominated that year so these two men truly did the Lord’s work. Second, it's probably the best use of PYT by Michael Jackson as a sample outside of the actual song. Finally, it just might be the happiest I’ve seen Kanye West in a music video. Good Life was truly good for all of us.
3. I’m n Luv (Wit a Stripper)
The song that started it all. I’m n Luv is so important because of its unexpected (and probably unintentional) crossover appeal. When the song was released in 2005, you were just as likely to hear the song in strip clubs as you were in the car of a soccer mom on Radio Disney. In a world that was getting used to the fact that hip hop was crossing the tracks into the suburbs, "I'm n Luv" was a song that all lifestyles of people could agree was a jam and a half. Plus it's off of his debut album which was appropriately titled Rappa Ternt Sanga. How can you not love that?
2. Bartender (ft. Akon)
If there’s one thing T-Pain loves for sure, it's a hard working woman that he can find at his local haunt. The song is one of the best examples of T-Pain's unique knack for storytelling and bringing listeners into the club with him. Could we call T-Pain the JK Rowling of the South? The Jack Kerouac of the strip club?
1. Buy U a Drank (ft. Yung Joc)
Before we had Trap Queen. Before Drake was fighting girls at Cheesecake. Before Kanye was Pablo, T-Pain was simply asking girls if he could buy them drinks at the club. Buy U a Drank was definitely the theme song for budding romances at middle schools around the country. If you didn't try to impress your date by showing them how good your snappin' skills were you either weren't trying hard enough or had already completed puberty by 2007. The song is peak T-Pain and when he gets his eventual BET Award show tribute, I hope that Jaden Smith does the Yung Joc verse.
BONUS: Thug Story ft. Taylor Swift
The world’s first reminder that Taylor Swift can’t be dealt with.