Club 520 Podcast – Bill Bellamy on Hooping with Penny Hardaway, Comedy Shows, and Meeting R. Kelly

Release date: January 5, 2026
Host: DJ Wells (with Jeff Teague, Bishop B Henn.)
Guest: Bill Bellamy

Episode Overview

This episode of Club 520 features veteran comedian, actor, and (as listeners learn) lifelong hooper Bill Bellamy. The crew dives into Bill’s basketball stories, iconic comedy era memories, thoughts on today’s NBA, and wild behind-the-scenes moments from his entertainment career—including a legendary R. Kelly story. The vibe is relaxed and hilarious, with Bill matching the hosts’ energy beat for beat.

Key Discussion Points & Insights

1. Bill Bellamy’s Hooping Credentials

• LA Fitness & Celebrity Runs:
  • Bellamy talks about still playing ball "relatively good" but jokes: "I ain’t really explosive like I used to be...now I’m jump shot, I’m mid-range, keepin’ it simple." (08:08)
  • Reminisces about high-level celebrity runs at Santa Monica College: Baron Davis, Paul Pierce, Nick Young, and "a few gang members mixed in." (09:11)
  • "If you lose, you be mad...you might have to wait like 5-6 games." (09:39)
• Best Hooping Celebrities:
  • "Off the top, Chris Brown...probably one of the most athletic guys that I didn’t know was that athletic." (10:05)
  • Flex Alexander and Tank—Tank "uses all his fouls in the first quarter," then sings to you. (10:19)
  • Jaleel White ("Steve Urkel") is surprisingly tough: "Jaleel is tricky because he’s kind of like unexpected quick." (11:00)

2. Classic Street Ball & East Coast Basketball Tales

• Rutgers Roots:
  • "We had John Battle, Roy Henson—made it to the NBA. Ray Rice in football…" (11:35)
• Street Legend Shoutouts:
  • The awe-inspiring "Ali Mo," described as 6'8", "blue black," unstoppable in summer leagues: "He was unguardable, it was a show in a show." (12:54)
  • Skipping at the Rucker: "They’d say, 'If you look at Skip, he gonna put you on the ground!'" (13:54)
• Legendary Summer League Game:
  • Talks about playing against Penny Hardaway, Larry Johnson, and Scottie Pippen at University of Maryland, and describes the day LJ hurt his back:
    "Grandmama was like the first LeBron, okay? ... Penny threw the alley, LJ caught it and went down. He never been the same." (16:41)

3. Comedy, Crowd Work & The 'Golden Era' of Black Sitcoms

• On Crowd Engagement:
  • "I love just being off the rip with it...if Jermaine Jackson or Deebo ever come to my show, stay in the back. If I can see you, I gotta say it." (22:06, 22:54)
• Reminiscing About Def Jam & Standup Legends:
  • "Martin didn’t even have to do his set—he was tearing motherfuckers up." (23:14)
  • "We got the best comedy class ever, bro...Dave, Chris, Sid, DL, Chris Tucker, Eddie Griffin, Steve Harvey..." (24:00)
  • On sitcoms: "We don’t have those same sitcoms like we used to...I think we could do it now; people want to see us." (25:22, 25:36)
• Comedy in the Internet Age:
  • "Does not mean you’re a comedian yet. You could be funny now...but that stage with a mic and a stool? That hit different." (47:54)
  • On social and standup stars: "Mojo Brooks, Desi Banks, DC Young Fly...they not cheating the game. They are talented, and they embrace their fan base." (49:42)

4. Memorable, Wild Club & Comedy Stories

• Jermaine Jackson’s Hair:

  • The crew and Bellamy roast Jermaine Jackson’s infamous hair (fro mistaken for paint).
    Bellamy: "It looked like the stuff do your roof with. You gotta heat that up—it’ll seal it." (19:12)

• Changing Comedy Norms:

  • On how today’s comedy is more restricted:
    "We can’t say nothing...Bernie Mac wouldn’t have made it...I feel like we should be able to laugh, as long as we not being disrespectful." (33:53)
  • Classic bit: “Back in the day, whatever was wrong with you used to be your nickname—cross-eyed Larry, club foot Willie, bowlegged Shirley…" (38:53)

• Short Women & Club Stories:

  • On seeing a short woman at the club:
    “I picked her up and put her on the counter...she said, 'thank you', everybody busted out laughing." (39:07)
  • “Back in the day, it was this one cute Puerto Rican little person...she might have caught me slipping.” (41:09)

5. Behind the Scenes of ‘How to Be a Player’ and His Acting Career

• Why Bill Made His Iconic Character Likable:
  • "The character wasn’t likable at first—had to make him charming and funny so women would want to watch." (41:59)
  • "How to Be a Player is basically the best day of your life. You get all the chicks, have the most fun, and bring your friends." (43:14)
• Cast Shoutouts & Legacy:
  • Names the cast (Bernie Mac, Natalie Desselle, AJ Johnson, etc.), reflects on their legacies.
  • "I have guys in their 20s, 30s, 40s, and 50s that watch How to Be a Player...that was almost 30 years ago." (44:20)
• Life Imitates Art:
  • "When I did the movie, afterwards, I went and got a loft—just like Dre [the character]." (47:04)

6. NBA: Then and Now — Hot Takes

• Favorite Current Players:
  • Guards: Anthony Edwards, Jayson Tatum, Steph, KD, Jalen Brunson, Darius Garland, Donovan Mitchell, Luka ("offensively, I think he’s unguardable, but he don’t play enough D for me." (60:50, 62:09)
• Jaylen Brown vs Luka Debate:
  • Bellamy: "If it’s not just about buckets, I’m going with Jaylen Brown." (62:39)
  • Explains importance of team play and defense:
    "Luka is all offense...but in playoffs, you gotta play D." (62:52)
• LeBron vs Jordan — Who’s the Real GOAT?
  • "LeBron is the goat of this decade...Michael Jordan is the goat of basketball." (66:21)
  • "Of the last 30 years, LeBron is the best basketball player I’ve seen." (67:05)
  • On starting a team:
    "You gotta go with Mike...but LeBron is magic, not MJ. Stop comparing him to Mike." (67:23)

7. Meetings with R. Kelly and Behind-the-Scenes Memories

• All-Star in Orlando, Hanging with “Rob”:
  • "R. Kelly bought Hennessy for the whole row...he was just such a good dude, very genuine. I used to hoop with him sometimes." (70:52)
  • "All the times I hung out with him, he was so dope...would get us all drunk, take us out." (72:08)
• In the Club When "I’m a Flirt" Comes On:
  • "Kells is at the end of the VIP, and when 'I’m a Flirt' came on, all the women got up. It looked like I was in the music video...I said, oh, I done made it!" (74:41)

Notable Quotes & Memorable Moments

"Grandmama was like the first LeBron, okay?...Size, athleticism...he was probably one of the most athletic three-fours at that time."
— Bill Bellamy on Larry Johnson (16:23)

"Back then, whatever was wrong with you used to be your nickname."
— Bill Bellamy (38:53)

"Mojo Brooks, Desi Banks, DC Young Fly...they not cheating the game."
— Bill Bellamy on new school comedy (49:42)

"The character wasn’t likable at first—had to make him charming and funny so women would want to watch."
— Bill Bellamy on playing Dre in How to Be a Player (41:59)

"Luka is all offense...but in playoffs, you gotta play D."
— Bill Bellamy (62:52)

"LeBron is the goat of this decade...Michael Jordan is the goat of basketball."
— Bill Bellamy (66:21)

"Kells is at the end of the VIP, and when 'I’m a Flirt' came on, all the women got up. It looked like I was in the music video..."
— Bill Bellamy (74:41)

Timestamps for Key Segments

• Hoop Stories & LA Runs: 07:56 – 11:00
• East Coast Streetball Legends: 11:35 – 15:05
• Penny/LJ Summer League: 15:35 – 16:41
• Jermaine Jackson’s Hair Roast: 18:21 – 20:15
• Comedy Crowd Work & Def Jam Era: 22:06 – 24:22
• Golden Age of Sitcoms: 24:22 – 25:36
• How to Be a Player: Behind the Scenes: 41:44 – 47:04
• Comedy in the Social Media Age: 47:54 – 50:17
• NBA Player Debates (Jaylen vs. Luka, LeBron vs. MJ): 60:41 – 67:23
• R. Kelly Stories: 70:52 – 75:38

Final Thoughts

This episode serves as a living oral history—Bill Bellamy’s infectious storytelling touches on the intersection of basketball, comedy, and Black pop culture from the ‘90s to now. The conversation is rolling with laughter, ribbing, and genuine respect, making it a must-listen—or, thanks to this summary, a must-read—for anyone who loves hoops, stand-up, or the art of a good story.