Jeff Ross wants to break through the political din.
Jeff Ross wants to break through the political din.
Courtesy Comedy Central

Is Jeff Ross the Most Important Political Comic in Trump's America?

Jeff Ross’s leafy backyard is usually tranquil. On an afternoon in spring, that's not the case: A backhoe is demolishing the house next door. Birds call nervously overhead. Cracks and booming thuds reverberate through the fence. Ross' own three-bedroom home will be the next to go, making room for a McMansion spanning both lots.

He mutters at the din and thumbs through his photos. Five nights ago in Brownsville, Texas, Ross filmed a free outdoor comedy show along the Mexican border wall for an estimated 700 attendees. The week before the taping was intense. He stops on an image of a heavily pregnant woman who'd just arrived in America. Others show a human-smuggling “coyote,” bandanna over his face obscuring his identity; an ICE vehicle ride-along; a toy dog abandoned in Rio Grande dust.

It’s too chaotic to talk. The toppling home, the deafening noise, the communication difficulties — metaphors for the political din his new special aims to break through.     

“Everybody’s just preaching to the converted: Liberals talk to liberals and conservatives talk to conservatives,” Ross says a few months later. “We made our case that we’re not going to mock or humiliate anybody on any side of the issue, and we’re going to try to do something objective but also deeper than most news reports that you see.”

Jeff Ross Roasts the Border: Live From Brownsville, Texas debuts Thursday, Nov. 16, on Comedy Central. Equal parts stand-up show and social documentary, Border challenged Ross to research, listen and shed any preconceived notions.

“Why don’t people just try to apply for citizenship, quote ‘the right way’? Why don’t they sign up for legal status?” he asks. “You start to see how dangerous it is and how long it takes. The people I met coming over the border from Honduras and El Salvador — where the murder rate per capita is through the roof — they’re not leaving; they’re not immigrating. They’re escaping.”

As the Friars Club's “Roastmaster General,” Ross has poked fun at celebrities for decades. On 2011’s Comedy Central Roast of Donald Trump, Ross took on 45’s hair, family members and reality contest The Apprentice. The president has even said Ross is his favorite comedian. Following the 2016 election, Ross shies from the praise.

Border addresses immigration policy and blind nationalism; it also chastises Trump: “If we let all the undocumented people just stay, it would help our economy over 10 years by over $1 trillion, 160,000 new jobs every year.” Ross explains. “If only we had a businessman who became president that could help us figure that out.”

Above all, Ross fosters a sense of empathy. By embracing the shortcomings that make individuals unique, he empowers viewers to identify and confront their own deep-seated prejudices and flaws. Ross uses humor to unite people, about as subversive an act there is in a media climate awash in alternative facts and confirmation bias.

Is Jeff Ross the Most Important Political Comic in Trump's America?EXPAND
Courtesy of Comedy Central

The 2005 documentary Patriot Act: A Jeffrey Ross Home Movie followed his experiences performing for American troops in Iraq. (Having worked with the USO for 15 years, last month Ross was named Ambassador of Veterans Outreach for the Artists & Athletes Alliance.) In 2009, he published the memoir/roasting how-to manual I Only Roast the Ones I Love. Ross was the guest on that September’s inaugural WTF With Marc Maron podcast, returning last April for the podcast’s 800th episode.

"There is something about Jeff’s style that transcends time and arcs across the expanse of comedy dating back to the Borscht Belt," Maron says. "He’s a comedy constant. He’s also a sweetheart." 

2015 special Jeff Ross Roasts Criminals scrutinized mass incarceration, while 2016’s Jeff Ross Roasts Cops sought common ground against the heated backdrop of Black Lives Matter. Both were timely, innovative showcases that not only entertained but informed. Above all, they humanized their subjects.

Since 2014 Ross has been adviser and lead judge of Roast Battle, a one-on-one competition pitting comedians in a battle of insults. What began as a sparse Comedy Store open mic now sells out weekly, in four years attracting celebrity judge panelists such as Jimmy Kimmel, Snoop Dogg and Seth Rogen.    

Ross recently welcomed Dave Chappelle back to the cramped, eardrum-bursting Belly Room, where Chappelle first scolded Roast Battle contestants for “all the puns — I hate puns!” One round later he’d stripped to his white tank, leapt up to dance and laughed, “OK, ya got me! Roast Battle made me like puns again!”

The show is a defiant response to the restrictions of political correctness and it maintains an unfolding purpose, bringing together disparate comedy genres and “scenes” in the pursuit of writing the best jokes possible. Men, women, trans performers, the mentally and physically challenged, comics of all ethnicities and beliefs enjoy a level playing field. It feeds off community, supportive energy and personal redemption.

Roast Battle is a coming-together of sorts that allows people to compete as equals regardless of their backgrounds. It's not so different from the immigration-assimilation experience Ross now tackles.

“Roasting is insult comedy that’s done with love,” he reiterates. “Laughter brings people together, and if you’re willing to open up for an hour or two, it could be really healing and powerful and enlightening.

“I have a lot of respect and admiration for the immigrant experience. We’re losing sight of the fact that, except for the Native Americans, we all have ancestors who came from somewhere else in search of a better life. So I’m begging our elected officials to be more compassionate in writing your speeches and laws, and just don’t forget that this is a nation of immigrants.”

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