Club Shay Shay – T-Pain Part 2 with Shannon Sharpe

Release Date: November 26, 2025
Host: Shannon Sharpe
Guest: T-Pain

Episode Overview

In this candid and entertaining follow-up conversation, NFL Hall of Famer Shannon Sharpe welcomes iconic artist T-Pain back to Club Shay Shay. The two dive deep into the realities of the music industry, T-Pain’s 20-year journey, lessons in business and friendship, catalog sales, creative process, Internet fame, and family. T-Pain pulls back the curtain about what truly matters to him and how he's navigated stardom, reinvention, and personal fulfillment.

Key Discussion Points & Insights

The Truth Behind “Buy U a Drank” and Music Business Lessons

• T-Pain explains why he didn’t make as much as expected from his classic hit (“Buy U a Drank”) due to sampling and publishing rights:
  • Paying homage to other artists’ lines led to ownership issues.
  • “I thought I was paying homage...the people that could take advantage of it, they take advantage of it.” (T-Pain, 03:30)
  • Labels/publishing companies—not the artists themselves—claimed shares.
• Performance remains lucrative:
  • Despite losing publishing/master ownership, T-Pain says he makes “$100,000 a night” performing the song live—far exceeding what publishers earn.
  • “While they were making 8 cents every three months, I was making 100 grand a night off of performing it.” (T-Pain, 03:58)

The TikTok Effect and Delayed Recognition

• Songs, including “Club Husband,” sometimes go viral years after release thanks to TikTok—even songs T-Pain himself wasn’t fond of:
  • “I hate it. That was the worst.” (T-Pain, 06:12)
  • He likens it to a relationship where you put in all the effort but the praise comes years later, when you've moved on.
    • “Why didn’t you say it then? You know how much power I put into that...and now you want to have a good time?” (T-Pain, 07:15)
• The frustration: Social media can create sudden value he can't predict or control, and sometimes others profit off leaked music.
  • “This nigga said, hey, I stole your shit and made money off of it. So you need to give me money now.” (T-Pain, 08:57)

20 Years in the Game: Hard Realities About Relationships

• Shannon asks about lessons from T-Pain’s two decades in music:
  • “Nobody is your brother. Nobody.” (T-Pain, 11:21, 15:04)
  • Artists often promise loyalty, but few reciprocate; T-Pain has learned to focus on who adds real value, not empty “brotherhood” talk.
  • “I'd rather you tell me what the business was and not have the brother aspect in there...Let’s do it again. I’d rather know the plan than to say you my brother.” (T-Pain, 15:51)
  • Memorable analogy: Shannon’s “python story”—warning how some friends seem caring but are just “sizing you up” to take advantage (19:21–20:01).

Removing Fake Friends and Outgrowing “The Feature King” Era

• T-Pain is direct about cutting off those who treat him transactionally.

  • “You make it very obvious...No, I am not [available].” (T-Pain, 21:03)
  • As he’s grown, he values honesty over forced friendships, realizing some connections were just business.

• During his feature-heavy peak, some artists didn't want him in their videos to avoid association if his style faded.

  • “Just in case the thing I was doing was a gimmick and they can separate themselves from me later on...It didn’t work out their way.” (T-Pain, 23:27)
  • Now, T-Pain’s identity is his own: “It’s just me and my wife.” (T-Pain, 24:24)

Why T-Pain Sold His Catalog

• Shannon presses on the decision to sell his hits:

  • The lump sum offered was equal to “100 years’ worth” of earnings.
    • “Why would I sell y’all this? [They said,] ‘We’re gonna give you 100 years’ worth of money right here, all at once.’” (T-Pain, 25:09)
  • The deal is a partnership (with HarborView), letting them claim future projects but also infusing major up-front cash and opportunity for new collaborations (27:10–28:56).

• First major purchases:

  • A 50,000 square foot building “for all my businesses.”
  • A plane.
  • T-Pain’s wife stayed low-key, wanting “some black shirts.” (30:44)

Early Hustle and DJ Perspective

• Started as a 14-year-old DJ, carrying crates to gain club entry.
  • Learned what makes songs hit by observing DJ crowd reactions.
    • “The reason I can make the songs the way I make [them] is because I was hearing the songs that DJs were playing...and I started studying why people like the parts of songs that they like.” (T-Pain, 35:24–36:45)

Bad Investments and Lapses in Financial Awareness

• Reports buying a Bugatti with his last money, not knowing it; careless investments (e.g., $150K on his granddad’s “sagging jeans” invention that never launched).
  • “When I bought that Bugatti, that was the last bit of my money, and I had no idea.” (T-Pain, 37:32–37:44)
  • Now, he’s vigilant: “If somebody tries to send $4 from one of my accounts, I get an alert.” (38:38)
  • Missed out on fashion trends he was ahead of, like pants with built-in boxers, later sold by Balenciaga. (39:30–40:45)

Streaming, Twitch, and True Transparency in Creation

• T-Pain creates all his music live on Twitch now.
  • Fans see every step from “first sound to release.”
  • “If your favorite artist ain’t doing the whole process, then what y’all watching this for, right?” (T-Pain, 41:04)
  • Open process highlights authenticity against today’s AI- or ghostwritten music climate. (44:56–45:02)
  • He enjoys the creative split between “drunk T-Pain” for ideas and “sober T-Pain” for finishing touches.

On Auto-Tune and Artistry

• Why he chose Auto-Tune:
  • To set himself apart, referencing Roger Troutman who also masked his natural singing voice for uniqueness.
    • “If you’re just gonna sing, just gonna be another singer...why put yourself in that category when you have the opportunity to set yourself apart?” (T-Pain, 49:37)

Genre-Bending and Vocal Talent

• Shannon asks if T-Pain would pivot genres à la Beyoncé.
  • Connects the roots of R&B, blues, and country, noting African American community’s deep influence. (50:08–51:16)
  • His cover album “On Top of the Covers” showcased his real singing voice, surprising most fans.
    • “I didn’t prove a point, but it was just like a, ‘See, I can really sing.’” (T-Pain, 52:19)
  • Crowdsourced song selection for a future covers project.

Writing & Giving Back

• Used to crave credit as a songwriter for others but now chooses satisfaction and financial reward over public acknowledgment.
  • “I had to learn to stop wanting to be in front of the camera.” (T-Pain, 54:56)
• Continues to give away “T-Mixes”—free features for songs he genuinely loves. (56:10)

The Masked Singer Experience

• Tried to drop out three days before but stuck with it (and won).
  • “Every night I was performing blind and I couldn’t see shit.” (T-Pain, 59:01)
  • Had to learn how to breathe differently for the “Madonna mic” and sang “Stay With Me” holding his breath to avoid audio issues.

Defining Success & What Matters Most

• T-Pain’s proudest achievement isn’t musical:
  • “My wife love me, and my kids don’t hate me, because I know so many that that is not the case.” (T-Pain, 61:42)
  • Cherishes genuine happiness at home, rejecting stereotypes of unhappy families.
  • “I can literally go broke tomorrow...but I’m still rich as [hell] because my kids and my wife love me.” (T-Pain, 64:23)

Notable Quotes & Memorable Moments

On Industry “Brotherhood”

“Nobody is your brother. Nobody.”
— T-Pain (11:21, 15:04)

On Outgrowing the Need for Credit

“I had to learn how to stop wanting to be in front of the camera...I did help your favorite artist. I did write this country song, I did write this shit...But I don’t need that credit.”
— T-Pain (54:56)

On Selling His Catalog

“We’re gonna give you 100 years’ worth of money right here, all at once.”
— T-Pain (25:09)

On Family

“My wife love me, and my kids don’t hate me...That is such an accomplishment for a black man that it’s—I mean a [man] can really be like, ‘T-Pain, your mama a hoe.’ Yeah, my wife love me, though...I can literally go broke tomorrow. I can lose all my money tomorrow. But I’m still rich as [hell] because my kids and my wife love me.”
— T-Pain (61:42, 64:09, 64:23)

Important Timestamps

• [02:34] – T-Pain addresses not making money from “Buy U a Drank”
• [06:10] – Expresses frustration about TikTok delayed success
• [11:21, 15:04] – “Nobody is your brother” in the business
• [17:15] – Lessons on who to keep on your team
• [25:09] – Explaining catalog sale decision
• [35:18] – Early days as DJ shaped his creative approach
• [37:32] – Losing it all by buying a Bugatti
• [41:02] – Creation process transparency on Twitch
• [49:12, 49:37] – Reason for using Auto-Tune, citing Roger Troutman
• [52:19] – Reinforcing his natural vocal talent
• [54:56] – Letting go of the need for recognition as a songwriter
• [59:01] – Masked Singer technical struggles
• [61:42, 64:23] – His grandest accomplishment: a happy family

Tone & Style

True to both Shannon’s and T-Pain’s personas, the episode is fast-paced, brash, funny, sometimes raunchy, but ultimately honest and generous with wisdom.

Summary Takeaways

This episode offers an unvarnished look at T-Pain’s journey through stardom, betrayals, creative evolution, financial lessons, and above all, the importance of fulfillment at home. The music business is a minefield of shallow alliances—what counts are the family and real friends you keep close, the joy in creation, and the wisdom to cut off what doesn’t serve you.

For fans of music, business, or anyone chasing their own lane, this conversation delivers lessons and laughs you won’t soon forget.