Go Fact Yourself Ep. 181.5: The Best of Hip-Hop Special
Release Date: October 3, 2025
Hosts: J. Keith van Straaten, Helen Hong
Theme: A deep dive into some of the most memorable and insightful hip-hop moments from Go Fact Yourself, revisiting past episodes with legendary artists, producers, and comedians, exploring rap’s history, its influence, and the stories behind classic tracks.
Episode Overview
This "Best of Hip-Hop" special collects highlights from years of hip-hop-themed quizzes, interviews, and surprise expert cameos. The hosts focus on the genre’s rich history, key songs and personalities from the '80s, '90s and 2000s, its influence on pop culture, and firsthand accounts from iconic artists. The energy is celebratory and nostalgic, filled with legendary guests (DJ Jazzy Jeff, Speech, Big Daddy Kane, Spinderella, DMC, Candyman, and more) recounting stories behind classics and their enduring love for hip-hop.
Key Discussion Points and Insights
1. 1990s Hip-Hop Nostalgia with Gina Yashere & Billy Gardell
Segment from Episode 142
- Gina Yashere: Shares her love for '90s hip-hop, reminiscing about MTV Cribs, learning dance moves, and dreaming of appearing in videos with Public Enemy and Big Daddy Kane (00:30).
- Favorites named: Public Enemy, De La Soul, Queen Latifah, Missy Elliott.
- Quiz Segment: Focuses on Ahmad's "Back in the Day."
- Featured Expert: Ahmad, who described the making of his classic (09:50).
“All I could think of is like, back in the day, you know? … The last song on the album became, like, the song of my life.” – Ahmad (12:35)
- Ahmad reveals: He wrote it at 17, recorded at 18 (15:00).
- Current work: Now a counselor for high schoolers, filmmaker, and motivational speaker.
- Featured Expert: Ahmad, who described the making of his classic (09:50).
2. Arrested Development and the Legacy of Speech
Segment from Episode 121, with Yvette Dion & Sean Patton
- Yvette Dion: Expresses love for '90s and 2000s hip-hop, even without keeping up with younger rappers (23:25).
- Quiz: Based on "3 Years, 5 Months, and 2 Days in the Life of..."
- Featured Expert: Speech from Arrested Development (26:45).
"It was uncanny … making music, touring that music, meeting tons of new industry and non industry people … making money for the first time in our life." – Speech (30:14)
- Insights:
- Album title = time to get their record contract.
- Sampling Prince in "Tennessee" without legal clearance—a $100,000 lesson.
“At the time, I thought he was exorbitant ... But the truth is, he could have asked for writing credits. … So, to be honest, as time went on, I got it. Like, he actually did us a favor.” – Speech (34:29)
- Speech describes meeting Mandela after supporting anti-apartheid causes (38:20).
- Legal story about the "Arrested Development" TV show using their name.
- Chuck D referred the group to Spike Lee for the Malcolm X soundtrack (44:15).
- Featured Expert: Speech from Arrested Development (26:45).
3. East Coast 90s Hip-Hop with Big Daddy Kane & Spinderella
Segment from Episode 167, with Sarah Jones & Phil Rosenthal
- Sarah Jones: Performed at Nuyorican Poets Cafe; recounted Jay-Z being in the audience (50:18).
- Quiz: Name the duet song by Big Daddy Kane and Spinderella.
- Featured Experts: Both join live! (53:42)
“You came in the studio with your stomach poking out so big because you was pregnant at the time. … It was a beautiful night.” – Big Daddy Kane, recalling their collaboration (55:08)
- Reflect on 1990s as hip-hop's mainstream crossover.
- Spinderella: “With salt and pepper, we kind of helped that along … There’s nothing like it.” (59:02)
- Kane: On mentoring Jay-Z and upcoming projects ("Paragraphs I Manifest" documentary, memoir "Just Rhyming with Biz") (01:01:34).
- Spinderella describes her pivot into comedy and live events.
4. Will Smith’s Hip-Hop Career with DJ Jazzy Jeff
Segment from Episode 87, with Sean Devlin & Allison Libby
- Sean Devlin: Admires Will Smith’s jump from rapper/TV star to action star (01:07:49).
- Quiz: Name the Grammy-winning Will Smith album, its hit single, and collaborator.
- Featured Expert: DJ Jazzy Jeff (01:10:12):
“The Fresh Prince of Bel Air is the biggest rap song in history.” – DJ Jazzy Jeff (01:15:25)
- Early start as a DJ, world championships.
- Recounts Grammy boycott—leading to change in TV coverage of rap awards.
- The "Fresh Prince" theme song: “We recorded it, sent it in as a placeholder … that's the theme song. The exact crappy mix that I did is still on the air.” (01:13:55)
- Affection for Will Smith's talent and ambition.
5. Open Mike Eagle on Art Rap & Generational Change
Segment from Episode 165, with Paula Poundstone
- Discusses the inspiration behind album "Service Merchandise" and the embrace/haunting of "art rap" as a genre label (01:23:45).
- Open Mike Eagle: "The fun for me is trying to come up with novel rhymes, like rhymes that I feel like I came up with." (01:27:00)
- “Art rap” label was intended to distinguish experimental styles from mainstream—but now, "everybody's weird."
6. Hall of Fame Hip-Hop: DJ Jazzy Jeff and DMC
Segment from Episode 100, with Faith Saley
- DJ Jazzy Jeff: On the excitement of being part of hip-hop's inception: “It was a budding new culture that for the first time, I felt like somebody was making something specifically for me.” (01:33:10)
- Quiz: First two hip-hop groups in Rock & Roll Hall of Fame; who inducted Run DMC.
- Featured Expert: DMC (Darryl McDaniels) of Run DMC (01:36:42).
“I wore glasses. I was a straight A student … everything that was good about me … the world made me think, wanted me to think that I was worthless. But if y' all remember, when I started doing my hip hop records … Daryl is perfect just the way he is.” – DMC (01:40:45)
- Talks about his children's book "Darryl’s Dream" and the importance of self-acceptance.
- Reveals forthcoming collaborative track with Jazzy Jeff, Ice-T, Chuck D, and Bumpy Knuckles—video inspired by the Beatles' rooftop concert.
7. Capping Off with Candyman: “Knockin Boots”
Segment from Episode 176, with Jody Sweetin & Mark Evan Jackson
- Mark Evan Jackson quizzed on "Knockin Boots" details (name drops in lyrics, etc.) (01:48:51).
- Featured Expert: Candyman (01:51:10).
“The coolest thing about performing Knocking Boots is I can cheat my way through the performance because everybody knows it. Even if you forget something, you don't have to do nothing but just hold the microphone.” – Candyman (01:53:15)
- Reflects on the thrill of hearing his song honored by Casey Kasem—"coming in at number nine, Candyman, Knockin Boots. Man, I just sat there like, good God. It was a moment in time." (01:54:00)
- Still touring, marking 35 years of “Knockin Boots.”
Notable Quotes (with Timestamps)
-
Ahmad (on “Back in the Day”):
“I just wrote this hook, and the last song on the album became, like, the song of my life.” (12:35)
-
Speech (topic: Prince’s sample fee):
“At the time, I thought he was exorbitant ... But the truth is, he could have asked for writing credits ... So to be honest, as time went on, I got it. Like, he actually did us a favor.” (34:29)
-
Big Daddy Kane (on Spinderella collaboration):
“You came in the studio … so amazingly. It was a beautiful night.” (55:08)
-
DJ Jazzy Jeff (on “Fresh Prince” theme):
“I made the song in 15 minutes ... The exact crappy mix … is still on the air.” (01:13:55)
-
DMC (on childhood and hip-hop):
“I had a confidence in myself and believed in myself ... And Jeff knows this. People that didn't even need glasses wanted to wear glasses.” (01:40:45)
-
Candyman:
“If you ever need anybody. Yeah, he's number right now.” (01:53:15)
Timestamps for Major Segments
- 00:05 – Show opening, hosts intro, hip-hop nostalgia with Gina Yashere
- 09:50 – Ahmad joins, discusses "Back in the Day"
- 23:25 – Yvette Dion on 1990s/2000s hip-hop, Arrested Development segment
- 26:45 – Speech joins, Arrested Development stories
- 50:18 – Sarah Jones on East Coast hip-hop, Big Daddy Kane & Spinderella
- 53:42 – Kane & Spinderella join, behind the duet
- 01:07:49 – Will Smith expertise, DJ Jazzy Jeff interview
- 01:10:12 – DJ Jazzy Jeff on early career, Grammy stories
- 01:23:45 – Open Mike Eagle, art rap segment
- 01:33:10 – DJ Jazzy Jeff, Rock Hall of Fame, DMC joins
- 01:36:42 – DMC on confidence, “Darryl’s Dream”
- 01:48:51 – Mark Evan Jackson quizzes on Candyman, "Knockin Boots"
- 01:51:10 – Candyman joins, lasting impact of his hit
Tone and Language
- The episode keeps the lively, playful, and respectful spirit of Go Fact Yourself.
- The hosts show genuine fandom and curiosity, making room for joy and surprise when legends drop in.
- Experts themselves are honored, humble, reflective, and often delighted to be celebrated for their work and to see their cultural impact through the lens of new generations.
Conclusion
This “Best of Hip-Hop” special is a showcase of the genre’s multifaceted influence, from personal journeys to global pop culture. It honors not only legendary artists and producers but also the comedians and fans for whom hip-hop shaped their worlds. With insider stories, historical context, and heartfelt tributes, it’s a time-capsule journey through the genre's greatest moments, packed with sound bites, quiz show fun, and plenty of classic jams. Whether you’re an old-school head or a newcomer, this episode captures why hip-hop matters—and endures.