An epic rant on the NBA Playoffs, specifically people who have come up small or just gone straight missing.

Oliver is joined by Mylan, a video producer, photographer, and award-winning cinematographer. They get into a discussion on how Mylan got started as a photographer, his work in the Obama Photo Office and the NY Times, the politics of capturing and editing the White House, how a photo tells 1000 lies, working with individuals across the political aisle, his work with the 48 hour film project, competing in international film competitions, and much more.

In The Ring is back!! After a very long hiatus, Oliver is joined by Kaitlyn, an arts coordinator, artist, and professor at Tufts University. They discuss the sacrifice that artists make for their goals, the artist voice, art in the Trump era, the difference between "good" and "bad" art, using art responsibly to promote social causes, non-political art and art as therapy, racial social justice issues, and much more.

Oliver is joined by Terrell and Jordan as they discuss working in the service industry trenches, annoying things that customers do, differences in restaurant clientele, expectations in service, food and tipping for different customers, donating to break the stereotype of black people not tipping, perks of being a good tipper, big spenders on the restaurant scene, the hook-up scene in the service industry, wild stories from the restaurant scene, impact of immigrants in the restaurant industry, and much more.

Ben and Eliza are out and Oliver holds down the fort with Terrell and Mikey. They talk the NBA 2018 Free Agency with DeMarcus Cousins joining the Golden State Warriors, whether LeBron is to blame for the rise of Super Teams, the luck required for GSW to make the finals, LeBron going to the Lakers and the legacy of the Lakers, the NBA changing playoff seeding, the difference between LeBron and Michael Jordan, the upcoming NFL season, and a lot more. They also give their top 5 in the Modern Era of basketball.

The trio is joined by a friend of Ben’s, Brad. Brad is a Sommelier and a general manager at Haymaker, a local Charlotte restaurant. Brad provides education on the wine, where he teaches us about good/bad wine, finding good wines at affordable prices, differences different regions and years make on wines, buying wines based on the labeling, dealing with wine snobs that keep talking, learning how to pick a wine on a date, and much more. The trio also perform a wine tasting, where Eliza’s hate of Riesling is put to the ultimate test.

Oliver, Ben, and Eliza are back! They discuss President Trump's newly announced Space Forces military branch and the perks of joining. Eliza also poses a question of whether you could get paid to do nothing, whether more money makes more problems, people winning the lottery, fantasizing about winning the lottery, how a lot of money changes people and their lives, and much more.

The trio of Ben, Eliza, and Oliver return to discuss the recent mental health issues in the news. They discuss Anthony Bourdain, the impact of celebrity suicide on people, the lack of individuals of counseling among the rich and famous, the stigma around mental health counselor, the struggles of asking for help, dating people that are depressed/dealing with mental health issues, mental health in the gun debate, and much more.

In The Ring is in front of a live studio audience! Ben and Eliza are out, but Oliver is joined by Anna and Beth, two lawyers in a special edition of the podcast called "Lawyer's Only". The lawyers play a drinking game where every time the word law is said, people take a drink. The lawyers discuss the hell of law school, when they they realized they had regrets about being in law school, Oliver wearing a gorilla mask and sombreros for law school finals, the times in law school when you wanted to give up, dealing with gunners in law school, bar review and drinking in law school, making lifelong connections in law school, and the point where you let it all out in grad school. They also play Tap Out! You don't want to miss this!

Ben, Eliza, and Oliver discuss being positive and their dogs. They then discuss people coming to Ben for medical advice and not believing him, WebMD/Googling for their medical information, people arguing with Oliver about legal advice, whether people look for advice just to confirm what they already want to do, Oliver and Eliza give impressions of idiot clients, the act of genuinely seeking advice, and much more.