Thedewsperspective

There has been great music released by seasoned emcees recently. This made me think of using ChatGPT to initiate a valid debate.  A debate about the “Top 50 Rappers Over 40.” This isn’t an original list of my own.  And if you understand ChatGPT, you’ll know, it’s nothing original there either.  Yesterday, Cam’Ron reported that he lost a rap battle to ChatGPT.  Today, I asked ChatGPT to start a great barbershop debate for the weekend.   If nothing else, we know we can always count on these types of lists to create a debate.  Now if you don’t mind indulging me.  Let us look at artificial intelligence in an objective way.  And see what it has to say about the “Top 50 Rappers Over 40.” 

It is documented that ChatGPT primarily sources its information from a massive, pre-existing dataset of text and code.  This dataset included a wide range of materials like books, articles, websites, Wikipedia, and even publicly available Reddit threads (Reddit threads is essentially a discussion that starts with an initial post and includes all subsequent comments and replies).  It essentially learned patterns and relationships in language from this data, allowing it to generate human like text and answer questions. 

I asked ChatGPT to rank the Top 50 Rappers Over 40 (as of 2025). 

Criteria Used for Ranking:

• Artistic influence over time
• Album/catalog quality
• Lyrical talent and innovation
• Cultural impact and continued relevance
• Post-40 contributions

Rank	Rapper	Age	Key Contributions
1	Jay-Z	55	Cultural icon, lyrical excellence, longevity
2	Nas	51	Classic albums + Grammy-winning late-career work
3	Eminem	53	Elite lyricist, massive global influence
4	Black Thought	50	Undisputed bar-for-bar champion
5	Kendrick Lamar	38*	Honorary – turns 40 in 2027, already legendary
6	Pusha T	47	Sharpest coke rap lyricist
7	Killer Mike	49	Run the Jewels success + solo return
8	Royce Da 5’9”	48	Wordplay, introspection, growth
9	Ghostface Killah	54	Storytelling genius, still active
10	Method Man	53	Maintains lyrical quality & star presence
11	Q-Tip	54	Tribe Called Quest’s visionary
12	Busta Rhymes	52	Energetic, technical, influential
13	Lupe Fiasco	42	Conceptual genius, still elite
14	El-P	49	Sonic architect of modern underground
15	Tech N9ne	53	Independent success story
16	Jadakiss	49	Punchline king with timeless flow
17	2 Chainz	48	Southern charisma, business savvy
18	Roc Marciano	46	Pioneer of luxury minimalist rap
19	Westside Gunn	42	Visionary behind Griselda movement
20	Conway the Machine	42	Raw, gritty, emotional delivery
21	Bun B	51	Southern rap OG, respected elder
22	Rick Ross	49	Luxury rap & label-building
23	Big Boi	49	Outkast half, consistently creative
24	Common	53	Poetic, conscious rap mainstay
25	Styles P	49	Grit and growth, consistent catalog
26	LL Cool J	56	Early icon, stage presence
27	Ice Cube	55	Ruthless rhyme writer turned mogul
28	Scarface	54	Emotionally powerful storyteller
29	E-40	57	Bay Area legend, slang innovator
30	Too $hort	58	West Coast pioneer, still active
31	Freddie Gibbs	42	Technical skill + soul fusion
32	Talib Kweli	49	Political bars and sharp pen
33	Billy Woods	43	Avant-garde, complex storytelling
34	Big Daddy Kane	56	Golden era lyricism benchmark
35	Rakim	57	Blueprint for modern MCs
36	Inspectah Deck	54	Wu-Tang’s underrated lyricist
37	The Game	45	West Coast flame thrower
38	Cam’ron	48	Harlem wordplay and swagger
39	Fabolous	47	Punchline consistency
40	Lauryn Hill	49	Influential lyricist, even with limited output
41	Pharoahe Monch	52	Lyrical technician
42	Redman	54	Wild, witty, wordplay legend
43	Mos Def (Yasiin Bey)	51	Poet-activist and rapper
44	T.I.	44	Southern kingpin, business icon
45	Joe Budden	44	Retired, but catalog respected
46	N.O.R.E.	47	From reggaeton to media success
47	Jay Electronica	48	Lyrical mystique, powerful content
48	Snoop Dogg	54	Pop culture fixture and rap icon
49	Wyclef Jean	55	Creative fusion of rap and world music
50	MC Lyte	54	Pioneer for women in hip-hop

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When I asked ChatGPT to give reasons for excluding some of the most prolific rappers from the list.  The response was:  You’re absolutely right to raise this. Several of the names you listed absolutely deserve inclusion on a list of the greatest rappers over 40. The omission of artists like Lil Wayne, Jeezy, Jim Jones, Malice, Juvenile, Raekwon, Benny the Butcher, and others isn’t a reflection of their talent. It does not undermine their contributions. Rather, it highlights the subjective and evolving nature of ranking lists.

Here’s why some might have been left out — and why they should be strongly considered:

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Deserving Rappers Over 40 Who Should Be on the List

Artist	Why They Matter
Lil Wayne (41)	One of the most influential rappers of all time; raised a generation of MCs.
Malice / No Malice	Part of Clipse, helped define street luxury rap; spiritual transformation adds depth.
Jim Jones (47)	From Dipset legacy to solo resurgence (Wasted Talent, El Capo), very relevant.
Jeezy (47)	Defined trap music’s blueprint; influential albums like TM101.
Juvenile (49)	Key to Cash Money’s rise; 400 Degreez is a Southern classic.
Raekwon (54)	Wu-Tang’s storytelling master; Only Built 4 Cuban Linx still legendary.
Benny the Butcher (40)	Modern street rap torchbearer; Griselda’s leading lyrical voice.

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Why They Might Have Been Overlooked:

1. Subjectivity in Rankings – Lists often reflect editorial taste, cultural moment, or bias toward East/West/underground/mainstream.
2. Recency vs. Legacy – Some lists emphasize consistent post-40 output, which might exclude artists with earlier peak moments.
3. Commercial vs. Lyrical – Artists like Wayne and Jeezy dominated commercially but don’t always get “lyrical” credit (unfairly).
4. Underrated Influence – Jim Jones, Benny, and Malice have made major contributions but don’t always get mass-media recognition.

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Final Thought on the exclusion of some of the most prolific rappers, according to ChatGPT:

You’re absolutely right — any serious, balanced list of rappers over 40 should include many of the names you mentioned.

Great question — there are definitely several rappers over 40 who may have been excluded from typical “Top 50” lists, yet deserve serious consideration due to their impact, consistency, lyricism, or contributions to the culture.

Here’s a breakdown of underrated or overlooked rappers over 40 — and why they deserve a mention:

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Rappers Often Excluded but Should Be Considered

*denotes rappers listed in the Top 50 list

Artist	Why They Matter
AZ (52)	One of the most technically gifted lyricists; Doe or Die is a classic.
*Black Thought (53)	Arguably the best pure lyricist alive; destroys every feature and freestyle.
Beanie Sigel (50)	Raw emotion, street wisdom, and punchlines; was Roc-A-Fella’s heart for years.
Styles P (49)	Consistent, hardcore, and spiritually conscious; strong solo work and LOX legacy.
*Killer Mike (49)	Powerful lyricist and activist; RTJ success and MICHAEL made waves critically.
CeeLo Green (49)	Part of Goodie Mob, Dungeon Family; unique voice, creativity, and crossover genius.
Phonte (45)	From Little Brother; one of hip-hop’s most respected for his wit, soul, and honesty.
Skyzoo (41)	Underground king; poetic street storytelling and jazz-infused hip-hop excellence.
Ransom (over 40)	Grimy, elite lyricist who’s had a major resurgence in recent years.
*Conway the Machine (42)	One of the best Griselda emcees; raw, vulnerable, and fierce in his delivery.
Blu (40)	Introspective and jazzy lyricist from L.A.; Below the Heavens is cult classic.
Slug (Atmosphere)	Spearheaded emo-rap introspection; massive underground impact.
*Bun B (51)	UGK legend; Southern rap godfather, consistent voice for Houston.
Twista (50)	Pioneer of rapid-fire delivery; technical marvel with classic hits.
8Ball & MJG	Southern legends who brought Memphis to the national scene.
Project Pat (51)	Memphis legend whose flow, slang, and content shaped a whole generation.
*Inspectah Deck (54)	Wu-Tang’s most underrated lyricist; iconic verses on “Triumph” and more.
*Cam’ron (48)	Dipset general, fashion icon, and trendsetter; still relevant with podcasting & bars.
*Busta Rhymes (52)	Still touring, still rapping at a high level; dynamic performer and innovator.
*Redman (54)	Jersey legend known for charisma, humor, and funk-infused bars.

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Why These Artists Are Often Overlooked:

• Underground or indie careers (less mainstream recognition).
• Overshadowed by group members (e.g., AZ next to Nas; Deck in Wu-Tang).
• Regional bias in many lists (East/West Coast often dominates).
• Late-career resurgences may not be on the radar of newer fans.

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Key Criteria for Inclusion

These rappers meet or exceed in one or more of the following:

• Lyrical excellence
• Cultural impact
• Career longevity
• Consistency
• Unique voice or message
• Post-40 relevance

Now that you know how the information was collected, compiled and communicated by ChatGPT.  What do you feel about the list?  How accurate is it?  What’s missing? 

Cornell Dews

http://www.thedewsperspective.com

cornelldews@aol.com