This was the “let Mike cook” episode of 50 For 50. I asked Mike if he knew Prince’s career and life story second best only to Michael Jackson, and he said he knows Prince, MJ, and Stevie Wonder best.

I explained why I wasn’t a big Prince fan growing up, mostly having to do with how young my ears were for his fairly adult music. But the best thing about 50 For 50 for me is this project gives me the chance to go through albums of music that I hadn’t listen to before, or hadn’t listened to in a very long time.

I liked Purple Rain. But I don’t think I understood its incredible appeal. After this episode, I do now.

Listen above or find us everywhere else below.

• 🌐 Website: 50for50.net

• 🎙️ Apple Podcasts: 50 For 50: Life, Music, Friendship

• 🎧 Spotify: 50 For 50

• 📺 YouTube: @50_For_50

• ✍️ Mike’s Substack: Curmudgeonly Yours

• ✍️ GG’s Substack: The Cool Check-In

I liked the idea of having two shorter shows that supported the longer actual 50 For 50 episode. The Top 5 was an easy one because it was putting together a list, but in audio form. But I also wanted a show where we could review a current music documentary, book, show, or whatever else was related to music and the artists we were talking about. I’ve always loved Ad-Rock’s line from “The New Style” when he started that song by saying, “And on the cool check-in…”

What the hell is the cool check-in? I’m not sure. But it’s a dope line and I’ve always wanted to use it on a project. So I decided that we’d use that as the title of our third podcast within this project.

And then, I decided to start writing my own Substack. And I looked and looked for a title. And that title kept coming back to The Cool Check-In. But I couldn’t steal that. Not from 50 For 50. But I remembered that I had a second option to The Cool Check-In that I really liked. It was called The Dope Spot. And here we are. The Cool Check-In is now my personal Substack name and The Dope Spot is the new name of our podcast.

In this episode:

• Mike and I talk about John Mayer’s new single, “Tom and Jerry,” announced on his 49th birthday. John should’ve been a part of this podcast. If only he were one year older.

• We also talked about Jay-Z choosing himself to be the half-time act at the Super Bowl. That was always going to happen.

• Lastly, we talked about John Legend’s new album, Muse, produced by Pharrell Williams.

Listen above or find us everywhere else below.

• 🌐 Website: 50for50.net

• 🎙️ Apple Podcasts: 50 For 50: Life, Music, Friendship

• 🎧 Spotify: 50 For 50

• 📺 YouTube: @50_For_50

Our Top 5 John Mayer songs lists are different — Mike and I don’t rank the same ones — but between the two of us, you’ll hear classics like “Clarity,” “Belief,” “Assassin,” “Gravity,” and “New Light.”

We also play a few rounds of Rock With It/Stop With It with songs like “Daughters,” “Your Body Is a Wonderland,” “Waiting on the World to Change,” and “Who Do You Love” to see if we still rock with them, or ever have.

Listen above or check us out everywhere below.

• 🌐 Website: 50for50.net

• 🎙️ Apple Podcasts: 50 For 50: Life, Music, Friendship

• 🎧 Spotify: 50 For 50

• 📺 YouTube: @50_For_50

John, as an almost 30-year-old dude, was speaking to me as a 30-year-old dude, thinking about similar things that I was thinking about. It’s been one of my go-to albums over the years.

Mike and I had fun with this one.

You can listen above, or check us out at all the places below.

Website: https://www.50for50.net

Apple Podcasts: https://podcasts.apple.com/us/podcast/50-for-50-life-music-friendship/id1857746432

Spotify: https://open.spotify.com/show/0ADmN7bp4fXQzAZsnSuFQj

YouTube: https://www.youtube.com/@50_For_50

A Different World is back y’all. It’s pretty incredible that Netflix decided to re-boot (re-launch?) a show from the Cosby universe back when sitcoms ruled Thursday nights. But there might not be a better time than now, in 2026, when we need more culture on our screens.

Mike and I discuss the first two episodes of the new series and wonder where things may go. Might we see some Lisa Bonet?

SZA is an interesting artist for us to cover on 50 For 50. For one, she’s still young in the game and usually, we are covering artists with many albums under their belt. But when it comes to the best artists of the last ten years or so, she’s on a short list.

I personally didn’t know her history well, so the deep dive was fun. We go through Ctrl and compare it to SOS.

I also talk about how good she was in One of Them Days and how if she ever gets tired of the music stuff, I’m buying stock in her as a comedic actress.

Listen above or find us everywhere else below.

• 🌐 Website: 50for50.net

• 🎙️ Apple Podcasts: 50 For 50: Life, Music, Friendship

• 🎧 Spotify: 50 For 50

• 📺 YouTube: @50_For_50

• ✍️ Mike’s Substack: Curmudgeonly Yours

• ✍️ GG’s Substack: The Cool Check-In

We saved this episode for much later in the season of 50 For 50, both to distance it from our episode on Tupac Shakur, and also because only had a couple of albums to his name, and just one released while he was still alive.

But Mike and I have had the Biggie and Tupac conversation over the years being that we ourselves are physically on opposite coasts. Pound-for-pound (and I’m not talking about his physical weight), no rapper has had as big of an impact as The Notorious B.I.G.

We went deep on his short career, but even in the little time he with us, his impact was B.I.G.

Listen and watch: https://www.youtube.com/@50_For_50

Apple Podcasts: https://podcasts.apple.com/us/podcast/50-for-50-life-music-friendship/id1857746432

Spotify: https://open.spotify.com/show/0ADmN7bp4fXQzAZsnSuFQj

More from the show: https://www.50for50.net/

After tackling Madonna through the lens of one album for our 50 For 50 episode on Confessions on a Dance Floor, it’s time to zoom out. On this episode, Mike and I rank Madonna’s catalog, top to bottom.

We dig into the hits — “Vogue,” “Dress You Up,” “Into the Groove,” “Papa Don’t Preach,” and more.

Then we play a round of Rock With It / Stop With It on some of her songs that may not age as well as others. Do these hold up in 2026?

• “Like a Virgin”

• “4 Minutes”

• “Who’s That Girl”

• “Justify My Love”

• “Ray of Light”

We’ll tell you where we land — let us know your rankings and your Rock With It / Stop With It calls in the comments.

You can always find us here as well:

Listen and watch: https://www.youtube.com/@50_For_50

Apple Podcasts: https://podcasts.apple.com/us/podcast/50-for-50-life-music-friendship/id1857746432

Spotify: https://open.spotify.com/show/0ADmN7bp4fXQzAZsnSuFQj

More from the show: https://www.50for50.net/

We made this hard on ourselves.

50 albums for 50 years; that’s it.

We decided, okay maybe I decided, that the hook would be that we can’t do more than one album per year. So that’s how we get to a Madonna episode from a 2005 album that I think is very well regarded, but maybe not a top three pick for most Madonna fans.

But because of the way that Mike and I do our show, it kind of fits. Why? Madonna was the queen of the comeback. And this was yet another comeback album for her. It was a third decade album doing what she loves doing which is dance floor stuff.

So while this wouldn’t have been our top pick of Madonna albums to dig into, it still allows us to tell her story.

In this episode, we get into:

• Her real origin story:

• The MTV era

• Her movie career

• The full Confessions on a Dance Floor breakdown

• A Grammy Redux

• Our Dream Collaborator, Album Tiers, and GG's hot take

Listen and watch: https://www.youtube.com/@50_For_50

Apple Podcasts: https://podcasts.apple.com/us/podcast/50-for-50-life-music-friendship/id1857746432

Spotify: https://open.spotify.com/show/0ADmN7bp4fXQzAZsnSuFQj

More from the show: https://www.50for50.net/

On Monday at 10:00 a.m. Pacific/1:00 p.m. Eastern, Mike and I are going live with our next episode of 50 For 50. We’re covering Madonna’s career, specifically through the lens of her 2005 album, Confessions on a Dance Floor.

If you can’t join us live, you can watch the episode on our YouTube channel or listen on our audio feeds on Spotify and Apple Podcasts.

One of our favorites, Ne-Yo, dropped a new album, and it’s country-inspired. Mike and I dug in and found it to be very good and worth a listen. While we both wouldn’t put it on par with Year of the Gentleman, which we went into full detail on a prior episode of 50 For 50, it’s an excellent lean for him in 2026 and shows that the man still has chops.

Listen above, or you can watch the YouTube video below.

Watch on YouTube: https://www.youtube.com/@50_For_50

More from the show: https://www.50for50.net/

Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/50-for-50-life-music-friendship/id1857746432

Listen on Spotify: https://open.spotify.com/show/0ADmN7bp4fXQzAZsnSuFQj

Mike Joseph and I are back covering Solange’s A Seat At The Table.

We go over Solange’s musical journey from Solo Star and Sol-Angel and the Hadley St. Dreams years, her independent turn with the True EP, through her last two works (at least currently).

We cover A Seat at the Table itself in full detail. Listen here, or you can also find us on Apple Podcasts, Spotify, and YouTube.

Apple Podcasts: https://podcasts.apple.com/us/podcast/50-for-50-life-music-friendship/id1857746432
Spotify: https://open.spotify.com/show/0ADmN7bp4fXQzAZsnSuFQj
YouTube: https://www.youtube.com/@50_For_50

From there, the guys run a "Rock With It, Stop With It" round pulling deep cuts from both George Michael's solo catalog and Wham!'s discography — the songs that hold up versus the ones that haven't aged as well. The episode closes with a real conversation about George Michael's death: the coroner's finding of dilated cardiomyopathy, myocarditis, and a fatty liver, and just how much his health had actually deteriorated in the years before, from a near-fatal bout of pneumonia in 2011 through a string of hospital stays that followed.

This episode pairs with our full Faith deep dive, where Garrett and Mike cover George Michael's entire career: the Wham! years, the making of Faith, the Grammy history, and a full track-by-track dive on the album itself.

Listen and subscribe: Website: https://www.50for50.net Apple Podcasts: https://podcasts.apple.com/us/podcast/50-for-50-life-music-friendship/id1857746432 Spotify: https://open.spotify.com/show/0ADmN7bp4fXQzAZsnSuFQj YouTube: https://www.youtube.com/@50_For_50

From there, Garrett and Mike dig into Faith itself: recorded largely in Denmark for privacy, written and produced almost entirely by George Michael himself, and packed with seven singles — including four #1 hits, a feat matched at the time only by Michael Jackson's Bad. They cover the making of the record, the censorship fight over "I Want Your Sex," studio stories from the musicians who were actually in the room (including the Jimmy Jam & Terry Lewis remix that reshaped "Monkey"), and a full track-by-track breakdown.

The back half covers George Michael's Grammy history — the Faith Album of the Year win and the surprising snubs that followed — plus a look at his real-life collaborations with Aretha Franklin, Elton John, Queen, Whitney Houston, and more, and the debate over who his ideal dream collaborator would have been.

Listen and subscribe: Website: https://www.50for50.net Apple Podcasts: https://podcasts.apple.com/us/podcast/50-for-50-life-music-friendship/id1857746432 Spotify: https://open.spotify.com/show/0ADmN7bp4fXQzAZsnSuFQj YouTube: https://www.youtube.com/@50_For_50

It's less a definitive ranking and more a real argument about what actually makes a Timberlake song great — the Timbaland-and-Danja futurism of the FutureSex/LoveSounds era, the Neptunes' funk-pop chemistry, or the raw vocal moments that don't need a big beat to land. Mike and Garrett also run through the songs that just missed their lists, and — because no Justin Timberlake conversation is complete without it — each names his favorite *NSYNC song.

This episode pairs with our full Man of the Woods deep dive, where Mike and Garrett cover Timberlake's entire career: the *NSYNC years, the Justin-vs-JC Chasez solo race, the Pharrell/Timbaland production breakdown, and a full track-by-track dive on Man of the Woods itself.

Listen and subscribe: Website: https://www.50for50.net Apple Podcasts: https://podcasts.apple.com/us/podcast/50-for-50-life-music-friendship/id1857746432 Spotify: https://open.spotify.com/show/0ADmN7bp4fXQzAZsnSuFQj YouTube: https://www.youtube.com/@50_For_50

By the time Man Of The Woods rolled around in 2018, Justin Timberlake was riding a wave as one of America’s biggest multi-media stars, a wave that had run uninterrupted for almost two decades. He was a top-selling musician, respected by critics and fans alike, productions and collaborations with Jay-Z, Ciara, Madonna and Duran Duran made him a top choice behind the boards as well. His easy charm and good looks also won him favor as an actor on the big and small screens.

Man Of The Woods was the sound of that wave crashing into the shore. It’s a messy expedition of an album that aims for the type of roots/R&B crossover that his occasional collaborator Beyoncé (and everyone from Shaboozey to Post Malone to Morgan Fucking Wallen) would later hit pay dirt with. What should have been a slam dunk-after all, Justin is from Memphis and has roots in country as well as soul music (two genres that are more closely related than most give them credit for)- turns into a swing and a miss.

Who should shoulder the blame for Man of the Woods being the semi-disaster that it is? Part of that blame should lay with Timberlake himself. After all, he’s the one who conceptualized the album right? Never the strongest of lyricists, songs like “Supplies,” “Flannel” and “Montana” are as half-baked and basic as the simple titles indicate. We should also toss some of that blame onto Timberlake’s collaborators. Chris Stapleton (who should be able to make an album like this with one eye closed and one hand tied behind his back) doesn’t bring his “A” game on the awkward “Say Something.” Meanwhile, the much-anticipated reunion with Timberlake and producers The Neptunes is a massive dud. Pharrell and Chad are washed, to say the least. And the magic that powered many of the better moments from JT’s solo debut, 2002’s Justified, had clearly vanished in the decade and a half since.

Thankfully, the album has a handful of salvageable moments. “Morning Light” is a sweet duet with Alicia Keys (whose creativity seems to have taken a similar tumble in recent years). For whatever it’s worth, JT has exhibited a particular chemistry with women performers (his Rihanna collaborations all slap), and he and Keys meld together seamlessly. “Breeze Off The Pond” is the highlight of the Neptunes collaborations, with a great verse melody and bridge. So, Man of the Woods isn’t a total failure. It remains somewhat puzzling that what should’ve felt like such an easy fit for Timberlake came out the way it did, and I feel like with different collaborators and more focus on lyrical quality, this could’ve been a great roots/soul fusion album (truthfully, Cowboy Carter, despite its critical acclaim, wasn’t it either). Point to this album as the beginning of the end for Justin Timberlake as popular music’s Golden Boy.

On this episode of 50 for 50, Mike and Garrett trace Timberlake's full arc: the surprising Brian McKnight songwriting credit on Justified, the Timbaland-powered run through FutureSex/LoveSounds and The 20/20 Experience, and a full production face-off between Pharrell/The Neptunes and Timbaland across Timberlake's entire catalog — who produced more, who produced better, and where the two overlap.

The back half of the episode is a deep dive on the featured album, Man of the Woods — Timberlake's "modern Americana with 808s" experiment named after his son Silas. The guys go track-by-track, share studio stories from producer Danja and Chris Stapleton, cover the album's #1 debut despite mixed reviews, and close with Grammy wins, Grammy snubs, and the tiers — where does Man of the Woods actually rank against Justified, FutureSex/LoveSounds, and the rest of the catalog?

Whether you're a day-one *NSYNC fan or just here for the Man of the Woods discourse, this one's got the receipts.

Listen and subscribe: Website: https://www.50for50.net Apple Podcasts: https://podcasts.apple.com/us/podcast/50-for-50-life-music-friendship/id1857746432 Spotify: https://open.spotify.com/show/0ADmN7bp4fXQzAZsnSuFQj YouTube: https://www.youtube.com/@50_For_50

It’s hard to imagine that Brandy is in her late 40s. Yes, I know, we don’t necessarily need to talk about someone’s age. But 50 For 50 is about aging and growing and doing so with grace and wisdom. As Mike Joseph and I talk about some of our favorite artists and albums, one of the things that stands out is how hard celebrity and especially the music industry can be.

In 1998, Brandy was sitting on top of the world. She and Ma$e. But in 2026, she’s more known for the memories of what she’s done than anything she’s currently doing. Which is why, her memoir came out at the perfect time.

It was both a great reflection about who we remembered her as, as well as a look at how she got there and the steps she’s currently taking to live a fulfilling life.

On our Brandy playlist, Big Money gives you all the big hits and other songs that you may not be super duper aware of. You can listen on Spotify or Apple Music below.

Listen now:

🍎 Listen on Apple Music

Tracklist (20 tracks)

1. A Capella (Something’s Missing) — Brandy

2. I Wanna Be Down — Brandy

3. Sittin’ Up In My Room (from Waiting to Exhale - Original Soundtrack) — Brandy

4. Long Distance — Brandy

5. Angel in Disguise — Brandy

6. Full Moon — Brandy

7. Right Here (Departed) — Brandy

8. Who Is She 2 U — Brandy

9. Have You Ever — Brandy

10. Should I Go — Brandy

11. Almost Doesn’t Count — Brandy

12. When You Touch Me — Brandy

13. Top of the World (feat. Ma$e) — Brandy, Ma$e

14. It’s Not Worth It — Brandy

15. I Tried — Brandy

16. Slower — Brandy

17. Brokenhearted (feat. Wanya Morris) (Single Version) — Brandy, Wanya Morris

18. Missing You — Brandy, Tamia, Gladys Knight, Chaka Khan

19. Best Friend — Brandy

20. I Wanna Be Down (feat. Queen Latifah, Yo-Yo & MC Lyte) (Remix) — Brandy, MC Lyte, Queen Latifah, Yo-Yo

Expect the obvious contenders in the conversation — "Protect Ya Neck," "C.R.E.A.M.," "Liquid Swords," Method Man and Mary J. Blige's "All I Need" — alongside a few deeper cuts Mike and Garrett think deserve more credit. It's less a definitive ranking and more a real argument about what actually makes a Wu-Tang song great: the chemistry of the full Clan trading verses, or a member's solo record hitting its own singular groove.

In the back half, Mike and Garrett zoom out to where the Wu-Tang story stands today, more than 30 years after Enter the Wu-Tang (36 Chambers). That includes the group's farewell "Wu-Tang Forever: The Final Chamber" tour, RZA's pivot into filmmaking, new albums from Raekwon and Ghostface Killah, Method Man's run as a working actor, and how Ol' Dirty Bastard's son has stepped in to carry his father's legacy onstage.

This episode pairs with our full Enter the Wu-Tang (36 Chambers) deep dive, where Mike and Garrett cover the group's origin story, the business plan behind their historic multi-label solo deals, and a full breakdown of the 1993 debut.

Listen and subscribe: Website: https://www.50for50.net Apple Podcasts: https://podcasts.apple.com/us/podcast/50-for-50-life-music-friendship/id1857746432 Spotify: https://open.spotify.com/show/0ADmN7bp4fXQzAZsnSuFQj YouTube: https://www.youtube.com/@50_For_50

In 1993, nine emcees emerged from Staten Island, NYC’s oft-forgotten fifth borough, and staked their claim to hip-hop immortality. Wu-Tang Clan embodied nothing that had been seen in hip-hop before or since; a rap music Voltron dripping with street knowledge, charisma, lyrical dexterity, storytelling skills and production that was avant garde while still making heads’ necks snap. Enter The Wu-Tang arrived during an era when New York City still had most of hip-hop’s attention (The Chronic, released late in 1992, had just begun to turn the tide), and arguably was part of NYC’s last stand as rap’s epicenter (along with albums like Tribe’s Midnight Marauders and Nas’ Illmatic).

How can I even begin to describe the Wu-Tang ethos accurately? They are the hip-hop equivalent of New Edition. They are the East Coast N.W.A. (at least in terms of how they formed as a group and later split into individually legendary solo acts while occasionally reforming). They are 100% of their era–the references to comics and kung-fu could only come from kids who grew up in 1970s and 1980s New York City, when Saturday afternoons were equally split between cartoons, wrestling and Bruce Lee movies on TV. The dark NYC they (and those of us who lived in the city pre-Guiliani and Bloomberg) inhabit is almost hard to imagine in a post-gentrification Big Apple. Enter the Wu is a time capsule that’s generally only decipherable by those of us who are old enough, and were lucky (or unlucky) enough to share the same geography. Hell, even the (recognizable) samples and interpolations– Gladys Knight’s “The Way We Were,” Hall & Oates’ “Method of Modern Love”- are locked into a certain era of pop culture that makes Enter The Wu a Gen X classic.

Almost every emcee in the unit gets the chance to shine, which is truly shocking when you consider how many rappers are jockeying for air time, and one track is a solo showcase for the incredibly charismatic Method Man. While he’s widely considered the Wu’s MVP, you also gotta give props to Raekwon and Ghostface for their vivid storytelling skills on “C.R.E.A.M.” or the wildly creative and pointed verse GZA drops on “Protect Ya Neck.” Ol’ Dirty sprinkles his chaotic craziness throughout the album, and you can’t not give a hat tip to The RZA for a truly unique production style that intertwined soul classics, film dialogue and the slightly off-beat drum style that propelled what would later become neo-soul. There are clear precedents- RZA’s style is a little bit DJ Premier, a little bit Prince Paul and a little bit Erick Sermon circa Redman’s first album. But he spins it into something entirely his own.

It’s hard not to look at this album through the prism of everything that’s transpired in the three decades since, from RZA’s transition into film scoring to ODB’s untimely passing to Ghostface emerging as the Wu member with the most consistent solo discography. It can be argued that no subsequent Wu-Tang album-individually or collectively-has eclipsed the debut. But how can you top the escapades of so many hungry emcees at a peak time for NYC hip hop? Enter The Wu endures as one of hip-hop’s most highly regarded albums and has been incredibly influential for several subsequent generations of emcees.