The Toast: "The Hardest Working Man in Hollywood with Justin Sylvester"
Date: November 18, 2025
Hosts: Jackie & Claudia Oshry
Guest: Justin Sylvester (TV host, podcaster, formerly “The Lady Sitter”)
Episode Overview
This lively, celebrity-driven episode features Justin Sylvester, known as “the hardest working man in Hollywood,” in a candid and wide-ranging conversation. Jackie and Claudia delve into Justin’s career journey, TV industry gossip, balancing hustle with nightlife, and his insider take on evolving entertainment trends. Topics span his stint at "The Today Show," the fate of "Daily Pop," pop culture’s changing landscape, navigating fame and privacy, as well as current events like the Wicked premiere, Met Gala, and more. The episode also covers heartfelt advice in the “Dear Toasters” segment and closes with personal reflections and recurring comedic banter.
Key Discussion Points & Insights
1. Justin’s Career Trajectory and the “Lady Sitter” Legacy
[00:03-01:14]
- Claudia introduces Justin as “the artist formerly known as the Lady Sitter.”
- Discussion of how “Lady Sitter” became synonymous with Justin; even AI search engines attribute the phrase to him.
- Tease of a possible show revival:
Justin: “We’re working on a show about it right now.” [00:37]
2. Filling in at "The Today Show" and Industry Insider Thoughts
[01:26-02:48]
- Claudia posits Justin as the clear frontrunner for Hoda's replacement:
“You’re the hardest working man in Hollywood... They still haven’t announced you as the official cohost.” [01:27–02:05] - Justin explains why NBC is rotating big-name guest hosts and reflects on what the network seeks in morning personalities.
- Justin on diversity and bringing a fresh perspective:
“I’m also single and younger and gay and in the streets. They need that.” [03:33]
3. Making a Mark with "Daily Pop" & the Evolution of Entertainment TV
[04:54–07:52]
- Nostalgic memories of “Daily Pop” and its cancellation due to executive turnover despite strong appeal.
- Thoughts on early-morning TV and keeping shows relatable:
“Being interesting on TV is living your life and bringing something to the table.” [08:30] - A missed opportunity: Daily Pop could have thrived as a digital/streaming show.
4. Showbiz Grind: Early Mornings, Social Life, and Staying “Interesting”
[07:52–09:21]
- Justin balances late-night socializing with early TV obligations:
“Fuck that... you have not gotten out of your house, you haven’t had a dinner past 7:30...” [08:30] - Advice from Jeff Lewis (via Justin) about reality stars:
“When housewives quit their day job, it ruins them.” [09:21]
5. Real Housewives Longevity, Rotation, and Kyle Richards
[10:30–11:59]
- Justin proposes a presidency-like rotation for Housewives:
“Every three years, someone siphons out and someone new comes in...” [10:44] - Reflects on close friend Kyle Richards’ 15-year run and her difficulty stepping away.
6. Red Carpet Reporting: Names vs. Professionals
[13:22–15:59]
- Critique of networks casting celebrities as red carpet hosts rather than seasoned pros:
“When you get said name, you need to put someone next to said name who knows how to do the job.” [13:59] - The value of industry-insider knowledge and “hype man” dynamics.
7. On Being the Next Giuliana Rancic & Generational Shifts
[16:19–17:47]
- Claudia: “You really are this generation’s Giuliana Rancic...Is it as fun as everyone thinks?” [16:19]
- Justin: The money and glamour have changed, but personality now reigns:
“Opinion and personality was our bread and butter...but I’m jealous as can be because they were the glory days.” [17:17]
[Featured Topic] Wicked Movie Premiere & Insights
[24:28–25:43]
- Justin describes his interviews with Ariana Grande and Cynthia Erivo at the Wicked premiere.
- Movie review:
“It’s a little darker, it’s a little deeper. It really is a good movie...I love the second one.” [24:59] - Talks about his personal connection to the cast and details about seeing the movie twice.
8. Fame, Relationships, and the Need for Privacy
[26:05–27:56]
- Justin reveals he’s been in a relationship for over a year, but doesn’t share it online:
“If you have a hot man with a job who’s over six’ one...don’t fucking tell anyone.” [26:20] - Discussion on generational shifts in attitudes toward monogamy and privacy.
- Claudia: “Would you say you live to work or work to live?”
Justin: “I think I live to work.” [27:59]
9. Met Gala, Amazon, and Ethics of Wealth
[32:01–37:00]
- Conversation about upcoming Met Gala, the Bezos sponsorship, and celebrity activism.
- Justin on public outrage over billionaires:
“As long as I’m still ordering Sensodyne on fucking Amazon and it’s coming that day, I can’t be mad.” [34:24] - Lauren Sanchez’s Hollywood role and public perception compared to Meghan Markle.
10. Meghan Markle, PR, and Celebrity Strategy
[38:06–40:42]
- How Meghan navigates celebrity (and what she could learn from a “good gay friend”):
“She just needs exposure therapy...” [38:25]
“The only way out is through it.” [39:58] - Critiques Prince Harry for inadequately preparing Meghan for royal life:
“That’s your fucking job. Go protect your wife.” [39:16]
Notable Quotes & Memorable Moments
-
On balancing work and nightlife:
“Being interesting on TV is living your life...Get the fuck out.”
— Justin [08:30] -
On red carpet reporting:
“Every rapper in history, there has always been a hype man.”
— Justin [14:07] -
On celebrity privacy in relationships:
“People magazine is going to have to cut his head off for the wedding picture.”
— Justin [26:37] -
On celebrity public opinion & billionaires:
“I can't have outrage about somebody whose product I still actively use.” — Justin [34:38] -
On Housewives and work-life:
“When housewives quit their day job, they become so dependent on the show that it kind of ruins it.“
— Justin [10:04] -
On staying fresh:
“You need to be in charge of where and how you live.”
— Justin advising a Dear Toaster [65:40]
Timestamps for Important Segments
| Segment | Topic | Timestamps | |-------------------|------------------------------------------|----------------| | Introduction | Justin Sylvester, “Lady Sitter” | 00:03–01:14 | | Today Show Talk | NBC, Hoda replacement speculation | 01:26–03:42 | | Daily Pop | Career highs, digital TV | 04:54–07:52 | | Hustle vs. Nightlife | Living an interesting life | 08:26–09:21 | | Housewives & Jobs | Housewives rotation, Kyle Richards | 10:30–12:17 | | Red Carpet | Industry, celeb hosts vs. pros | 13:22–15:59 | | Wicked Premiere | Movie review, interviewing stars | 24:28–25:43 | | Love & Privacy | Relationships, social media boundaries | 26:05–27:56 | | Met Gala/Bezos | Billionaires, ethics, celeb activism | 32:01–37:00 | | Meghan Markle | Celebrity strategy, public scrutiny | 38:06–40:42 | | Cher, SNL & Pop | SNL, Cher’s career, celebrity docs | 42:33–48:21 | | Dear Toasters | Advice, relationships, life changes | 63:18–72:19 |
Dear Toasters: Advice Segment Highlights
[63:18–72:19]
-
Dilemma: Move for husband’s lucrative job despite being far from wife’s family?
Advice:
Justin: “Let go, honey...You lose, have you seen the news? 15x the money, take the lifestyle.” [64:11]
Claudia: “You're doing this for him, so you say, ‘Let me be the one to choose the house and the neighborhood.’” [66:04] -
Dilemma: Surprise Venmo after a friend’s birthday dinner
Justin: “I'm not mad at the Venmo—if the conversation happens upfront.” [67:19] -
Dilemma: Husband not sharing baby news or inviting friends to baby shower
Justin: “Straight men are weird. Doesn't mean he doesn't care.” [69:36]
Episode Tone & Takeaway
- Language & Feel: Unfiltered, witty, and affectionate, the tone shifts between showbiz gossip, career wisdom, and advice with inside jokes and candid, lively humor.
- For New Listeners: You'll gain a strong sense of Justin's personality, his place in Hollywood media, and how relationships and hustle shape his and the hosts’ lives. Expect hot takes on pop culture, heartfelt career stories, and honest advice.
Connect with Justin
- Instagram: @JustinASylvester
- Podcast: The Yesterdays with Blakely Thornton (new episodes every Tuesday)
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