The Rubin Report: The Difference Between Writing Jokes for Bill Maher & Donald Trump | Evan Sayet

Release Date: May 9, 2025

In this engaging episode of The Rubin Report, host Dave Rubin sits down with guest Evan Sayet, an accomplished author, comedian, and conservative speaker. The conversation delves deep into the transformation of liberalism, the challenges faced by conservatives in modern America, and the intricate relationship between politics and comedy. Below is a comprehensive summary capturing all key discussions, insights, and conclusions from the episode.

1. The Evolution of Liberalism and Conservative Thought

Evan Sayet begins the discussion by reflecting on the decline of traditional liberalism. He emphasizes that true liberalism, which advocated for individual freedoms and democratic values, has shifted so far left that it now resides to the right of center. Sayet articulates this transformation by stating:

Evan Sayet [00:27]: "...how do you look at the Middle East and decide the problem isn't the homophobic, xenophobic, misogynistic Islamic fascists? The problem's a tiny liberal democracy of Jews."

Rubin probes further, questioning why "good liberals" failed to counteract these shifts:

Dave Rubin [00:42]: "Why were the good liberals unable to push back against any of this?"

Sayet attributes this failure to aggressive leftist movements that systematically "cleansed the schools and the entertainment industry," combined with natural generational attrition. He recounts historical attempts by radicals in the 1960s to overthrow Western civilization, which ultimately failed because people recognized the relative prosperity and safety of America compared to other parts of the world.

Evan Sayet [04:08]: "They went underground and they went on what's called the long march through the institutions... They use the institutions to brainwash successive generations into being those warriors that they, they couldn't get earlier because they were educated by the real world."

This "long march" strategy has led to leftist dominance in academia, journalism, education, and entertainment, shaping societal norms and values over generations.

2. Writing for Bill Maher vs. Donald Trump

A significant portion of the conversation centers around Sayet's unique experience of writing for both Bill Maher and Donald Trump. Sayet proudly notes:

Evan Sayet [00:54]: "I'm proudly the only person in the entire world who's written for both Maher and Trump."

Rubin is intrigued by the dichotomy and asks:

Dave Rubin [00:58]: "Tell me the difference between writing for Bill Maher and writing for Donald Trump."

Sayet explains that while Maher consistently delivered his written material effectively, Trump often deviated by adding unsolicited remarks, making it challenging for Sayet as a craftsman to maintain the integrity of his jokes.

Evan Sayet [11:28]: "Maher would more often say what I wrote... Trump said a lot of things I didn't write in between. It's heartbreaking and difficult sometimes."

Rubin adds a personal touch by sharing his experience of collecting insults from the President, highlighting the friction between their viewpoints.

3. The Decline and Future of the Democratic Party

The discussion shifts to the current state of the Democratic Party, which Sayet describes as a "party of negation." He criticizes the party for focusing solely on what they are against rather than presenting affirmative policies:

Evan Sayet [13:35]: "You never hear anything in the affirmative from the political left. You only hear, he's a Nazi, he's a fascist, he's a homophobe, he's a xenophobe."

Sayet argues that this strategy has led to a lack of positive vision, making the party vulnerable to internal collapse or takeover by radicals. He envisions a future where conservatives must unify and reclaim the Republican Party from mislabels like "RINOs" (Republicans In Name Only).

Evan Sayet [16:47]: "Ultimately what needs to happen is for every sane person to come over to become a Republican... We cannot have a party with any chance of power that hates America."

4. The Intersection of Politics and Comedy

Sayet and Rubin explore how comedy has become increasingly political. Sayet reminisces about the days when comedians like Johnny Carson provided news through humor without overt partisanship. However, the fragmentation of media channels has led to siloed audiences, preventing a unified comedic discourse.

Evan Sayet [10:42]: "Now we have so atomized our delivery system... Very little chance that one of my ideological cohorts is going to be watching the Stephen Colbert show."

Rubin laments the loss of apolitical humor, feeling that modern comedy has lost its ability to bridge political divides.

5. The State of Hollywood and Political Correctness

The conversation turns critical of Hollywood, which Sayet believes has succumbed to political correctness and lost touch with mainstream audiences. He cites the failure of studios to produce faith-based films despite their commercial success, attributing this to a desire to promote a utopian vision devoid of traditional values.

Evan Sayet [22:40]: "Hollywood doesn't want to make popular movies... They have to be smarter than us. And the only way to be smarter than us, better than us, is to not give us the values we want to share."

Rubin observes that there's a slow shift, but major studios like Disney continue to make the same mistakes, resisting change despite clear audience demand for more relatable content.

6. Deprogramming and Reversing Leftist Influence

Addressing the entrenched leftist ideology, Sayet emphasizes the importance of deprogramming individuals indoctrinated by mainstream institutions. He points out that modern liberalism equates thinking with bigotry, leading to indiscriminate moral imperatives.

Evan Sayet [29:49]: "Thinking was outlawed in the 1980s, because thinking is now seen as an act of bigotry... In order to eliminate discrimination, they must be utterly indiscriminate."

Rubin asks for strategies to "deprogram" those sold a set of "obvious lies." While Sayet begins to address this, the provided transcript cuts off before he elaborates fully on his methods.

7. Reflections on the Past and Present Political Landscape

Towards the end, Sayet and Rubin reflect on how America has changed, especially with the rise of social media amplifying extreme viewpoints. Sayet notes that the "WOKE movement" has become more entrenched and pervasive, making it harder to find alternative voices.

Evan Sayet [18:25]: "It's far less crazy because the WOKE movement hadn't yet so totally metastasized... It's crazier now because the craziness is more instantly delivered and it's impossible to escape."

Rubin expresses nostalgia for pre-social media times when political situations might not have felt as intense, although Sayet counters that the fundamental issues remain deeply rooted.

8. Closing Remarks and Future Outlook

As the episode wraps up, Sayet shares a personal anecdote about the first joke he ever sold to Rodney Dangerfield, highlighting his long-standing involvement in the comedy and political spheres. He underscores the necessity for balanced political discourse and warns against the dangers of a one-sided political landscape.

Evan Sayet [27:00]: "No one became quite as big as Rodney... They see us as so evil because we are the antithesis of their utopia."

Rubin and Sayet agree that restoring a healthy tension between political ideologies is crucial for a pluralistic society, avoiding the pitfalls of extreme dominance by any single perspective.

Notable Quotes:

• Evan Sayet [00:27]: "How do you look at the Middle East and decide the problem isn't the homophobic, xenophobic, misogynistic Islamic fascists? The problem's a tiny liberal democracy of Jews."

• Evan Sayet [11:28]: "Maher would more often say what I wrote... Trump said a lot of things I didn't write in between."

• Evan Sayet [16:47]: "Ultimately what needs to happen is for every sane person to come over to become a Republican."

• Evan Sayet [22:40]: "Hollywood doesn't want to make popular movies... They have to be smarter than us."

• Evan Sayet [29:49]: "Thinking was outlawed in the 1980s, because thinking is now seen as an act of bigotry."

This episode of The Rubin Report offers a thought-provoking examination of the shifting political landscape in America, the role of comedy and media in shaping public opinion, and the challenges faced by conservatives in reclaiming their narrative. Evan Sayet's insights provide a critical lens through which listeners can understand the complexities of modern liberalism and the importance of preserving democratic values.