CHIBOYJIMMY, BRENDA, and JAYE
Won To Won Podcast
Urban news from the minds of CHIBOYJIMMY and JAYE.
Author
CHIBOYJIMMY, BRENDA, and JAYE
Category
Podcast website
Latest episode
Feb 24, 2026
Where to listen?
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Episodes
The Criteria for Getting Flewed Out | WON TO WON PODCAST 24.02.2026 26:01
On this episode, the crew vibes out with their guests, Radio host JaeWithTheJuice and dessert chef Paige, as they discuss their views on men getting flown out. They compare the differences between men buying flights and women buying flights, the expectations they hold for the person getting flown out, and the stigma of the obligation of sex. Have you ever been flown out before? Do you buy flights...
Is Diddy Going Down? | WON TO WON PODCAST 24.02.2026 43:56
On this episode, the crew vibes out as they try to react to the new evidence in the Diddy Sex Trafficking Trial. They watch a news report and express their opinions about it. From their own personal experiences to finding empathy for Cassie and the other victims, the crew tries to break down and make sense of all of the allegations and show their support. Do you think #diddy should stay in jail? H...
The Double Standards of Dating | WON TO WON PODCAST 24.02.2026 23:30
On this episode, the crew vibes out with their guest, media expert JWalk (No Ticket) and they do a reaction to one of Malik B skits. They discuss the ins and outs of dating a girl that is popular, the respect needed to date in this era, and the double standards noted in the dating scene. Should men and women act the same when it comes to dating? Can men do things women can’t do? Who owes who respe...
Tricking 101 | WON TO WON PODCAST 24.02.2026 22:00
On this episode, the crew vibes out with their guest, media expert #JWalkNoTicket and they debate their thoughts on having a gay son or a thot daughter. They also do a reaction to a #pimpinken video that talks about the difference between pimping and tricking. Before you know it, they are giving a free lesson on the different levels of tricking. What do you consider as tricking? Is it a bad thing...
Is Tory Lanez Innocent? | WON TO WON PODCAST 24.02.2026 32:41
On this episode, the crew vibes out as they discuss the shooting of #Megantheestallion. There has been a revelation that might bring more evidence to the case. The crew reacts to a video of #torylanez lawyers discussing that new found evidence and Tory getting stabbed. Who do you think shot Megan? Do you think it’s a hoax? Should Kelsey go to jail? Should Tory be freed? What should Megan and her t...
They Not Like Us: Everyone Copies Black People’s Style | WON TO WON PODCAST 24.02.2026 13:45
On this episode, the crew vibes out with their guest, Media expert JWalk (no ticket) and they do a reaction to Asian men getting Black hairstyles. They debate the difference between original and copied, compare the way Black people and Asian people dress, and discuss their view on what culture is. They also dig into celebrities being free to hang out in their hometown. Should Asians wear locs? Are...
Fashion Takes From Men: Met Gala 2025 Review | WON TO WON PODCAST 24.02.2026 14:08
On this episode, the crew vibes out with their guest, Media Expert JWalk(No Ticket), and they react to the fashions of this years Met Gala. They go through the fashion do’s and don’ts, the best dressed, the worst dressed, and all the other things surrounding the Met Gala event. They also dipped into their celebrity crushes and who they would love to take on a date. This episode was full of laughs...
Women and The Phenomenon of Delusion | WON TO WON PODCAST 19.09.2025 29:59
On this episode, the crew vibes out with their guest, model Kandi, as they discuss their experiences with being delusional. They describe what their definition of delusion is and what it looks like. They dig deep into relationship views from a man and woman’s perspective. They also speak about how they feel about “tricking” on their significant other. Are you delusional? What do you think it means...
Should you support a Black Business? | WON TO WON PODCAST 19.09.2025 25:56
On this episode, the crew vibes out while doing a reaction to Wallo’s opinion about Black owned businesses. He said that if he likes the company he’ll support it, not just because the owner is Black. The Won to Won family discussed their experiences with Black owned businesses and how they think businesses try to connect with the Black community. Do you own a business? Should we support more Black...
Weird Teacher Stories | WON TO WON PODCAST 19.09.2025 23:31
On this episode, Jimmy and Jaye hold the fort down as they react to a TikTok video of a teacher being weird with his student. The Guys talk about their favorite teachers, their experiences with weird teachers, and how they would react if they were teachers. What makes a teacher weird? How should we handle teachers that don’t connect with children respectfully? Can we blame the parents for the bad...
Since That’s Your Career, I Can’t Date You! | WON TO WON PODCAST 19.09.2025 16:34
On this episode, the crew vibes out with their guest, model Kandi, as they discuss their thoughts on certain career choices. Having a job is great, but they explain that there are certain jobs they do not want their partner to have. Are truck drivers whores? Would you date a stripper? Can you trust a police officer as your wife/husband? Which career seems like a red flag to you? Watch this episode...
Are Sensitive Guys Weak? | Won To Won Podcast 19.09.2025 23:10
On this episode, the crew vibes out as they react to a clip from #tonightsconversation . A woman asked what should she do if her man is more sensitive than her? That question raised more questions from the Won To Won crew and gave them insight as to how they are within their personal relationships. Do you think men should show their sensitive side? How should women feel about their men crying? Wha...
Who has the best vocals in R&B? | Won To Won Podcast 19.09.2025 20:04
On this episode, the crew vibes out as they go through the list of the best vocalists created by singer Tank. They arrange the names in order and compare them to each other. Tank says Usher sings better than R. Kelly and Brenda & Jimmy agree while Jaye doesn’t. They thought of an R&B Verzuz and named who they think would win it. Do you think Tank’s list is valid? Is Chris Brown the best ma...
Understanding, Forgiveness, & Grace (Celebrities, Family, Friends, and Exes) | WON TO WON PODCAST 19.09.2025 23:28
On this episode, the crew vibes out as they talk about Chris Brown’s life in the limelight and his troubled past. They watched a video of David Banner speaking on the Grammy night situation and reacted to that. They compare and contrast Chris Brown to Suge Knight, Dr. Dre, Mack 10, BlueFace, and a few other well known artists. They also speak about personal experiences with abusive relationships a...
Can 100 MEN Beat 1 GORILLA?! | WON TO WON PODCAST 19.09.2025 21:28
On this episode, the crew vibes out while discussing the viral topic of 100 men fighting 1 Grown male Silver back Gorilla. Jimmy and Brenda think they all are going down while Jaye thinks he can beat the gorilla himself. Steve chimed in and the crew watched Gorillas in action on YouTube and even asked ChatGPT who winning in this battle. Who do you think winning? What type of men should be included...
Shannon Sharpe Sexual Abuse Lawsuit | WON TO WON PODCAST 19.09.2025 26:18
On this episode, the crew vibes out as they discuss their dating journeys, their experiences with younger and older people, and an update on the Shannon Sharpe sexual assault allegations. He is 56 years old and the only fans model is allegedly only 19. Is that reasonable or is it predatory? What is the age range you would date? Are cougars better than millennials? Should Shannon Sharpe pay the $50...
SINNERS RECAP (Slight Spoilers) | WON TO WON PODCAST 19.09.2025 29:46
On this episode, the crew vibes out while discussing the new Ryan Coogler film SINNERS. They dissect the story and the characters, the symbolism they noticed, and their own rating of the film. They kept the spoilers to a minimum, but the entire film was discussed. Did you see the movie? What do you rate it? Did you watch in IMAX? What do you think about the post credit scenes? Is this Michael B. J...
Black Men FLOCK To Europe To IMPREGNATE White Women | WON TO WON PODCAST 19.09.2025 21:21
On this episode, the crew vibes out with their guest, Chef Ricky, and they do a reaction to a TikTok video of Black men being intertwined with European women. It’s being said that Europe has been having mixers for Black men to come and meet their women to discuss relationships, marriages, and sperm donating. It seems as it’s a running joke at the moment, but it has been catching steam all over soc...
Has Black Dating Culture Evolved or Devolved? | WON TO WON PODCAST 19.09.2025 20:54
On this episode, the crew vibes out with their guest, Chef Ricky, to discuss the evolution of dating in the Black community. The crew does a reaction to a 1970’s sit down conversation between Black men and women about their experiences with dating at the time. Some things were extremely different from today, other things seemed truthfully wild. Who is the head of your household? Are you married? S...
If You Haven't Seen THESE Movies, Turn In Your BLACK CARD | WON TO WON PODCAST 19.09.2025 23:42
On this episode, the crew vibes out with their guest, Chef Ricky, to discuss their favorite Black Movies and the criteria for losing your Black Card. They went from Friday to Sinners, from The Cosby Show to That’s So Raven. Do you think there is a staple Black show? Should we create more Black centered shows and films? Which directors are on your watch radar at the moment? What makes a film or sho...
Seeing Your CHILD Born or Your FRIEND on his DEATHBED | WON TO WON PODCAST 19.09.2025 19:47
On this episode, the crew vibes out with their guest Chef Ricky to discuss the hypothetical situation of seeing your wife give birth or seeing your friend on his deathbed. The conversation takes a few turns and is filled with questions, answers, and a lot of laughter. Jaye and Steve picked their homie’s deathbed while the rest chose the wife and child. Overall everyone pleaded their cases and deba...
Who Had It Worse: SLAVES or JEWS? | WON TO WON PODCAST 19.09.2025 43:42
On this episode, CHIBOYJIMMY and CapJaye holds the fort down for Macdaddy Brenda as they discuss the correlations between The Holocaust and Slavery. The two men speak about the importance of remembering both tragical events, respecting each event, providing grace to the people of both worlds, and discussing the gravity each of the events has received. Although there are some differences, there are...
Anthony Edwards' Baby Mama: GOLD DIGGER or HONEST Woman? | WON TO WON PODCAST 19.09.2025 21:37
On this episode, the crew vibes out with their guest Chef Ricky to discuss Anthony Edwards’ family court issues. After giving birth to his child, Ayesha Howard looks to put the NBA star on child support, he agrees to pay all 18 years upfront and sign over his rights as a father. Do you think Ms. Howard is just a gold digger? Should they have worn protection? Is Anthony Edwards obligated to care fo...
Does THEFT Have an Age LIMIT? | WON TO WON PODCAST 19.09.2025 22:52
On this episode, chiboyjimmy and cap jaye hold the fort down for Macdaddy Brenda as they discuss the phenomenon of stealing. They share stories about stealing from their childhood, their thoughts about stealing today, and have a debate about the age limits for stealing. Have you ever stolen anything? What age is too old to be stealing? Should stealing be looked at as a huge crime? Watch this episo...
Influencers Like Ashton Hall Are TALENTLESS! | WON TO WON PODCAST 19.09.2025 34:49
On this episode, ChiboyJimmy and CapJaye hold the fort down for MacDaddyBrenda. They discuss the impact of influencers and do a reaction to Ashton Hall’s GRWM videos. Do you think everyone can be an influencer? Are influencers important to the culture? Should all celebrities have some sort of talent or meaningful interest? Who has the power to make someone famous? Which influencer is your favorite...
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