Chelsea Season 1, Episode 66: I Don't Want to Mess Up Again

Appetite for Instruction

Chelsea kicks off a whole new journey of discovery and delinquency with guests Drew Barrymore, Chris Martin and the U.S. secretary of education.

38 min

Gwyneth & Tony & Chelsea & TED

Chelsea talks lube with Gwyneth Paltrow and lobbying with Tony Hale, tests her acting chops in a telenovela, and learns the secret to an ace TED talk.

38 min

Dinner Party: Captain America & Friends

Chris Evans and the "Civil War" cast dish on superhero culture and Hollywood's blind spots, and Chadwick Boseman schools Chelsea on Black Panther.

34 min

Gwen Stefani, Tokyo Style & the Night Sun

Chelsea talks tour life with Gwen Stefani, steps out with a colorful Harajuku squad, and studies the moon with NASA's "Mohawk Guy," Bobak Ferdowsi.

35 min

Wanda Sykes & the 2016 Political Scene

Chelsea delves into the U.S. presidential race with comedian Wanda Sykes, former Obama speechwriter Jon Favreau and a posse of senior Florida voters.

34 min

Christina Aguilera & Chelsea on Ice

Chelsea reaches for a big note with the Grammy-winning "Voice" coach and steps into the rink with a pair of Russian figure skaters.

43 min

Barbara Boxer & Souls to the Polls

Senator Boxer and African-American churchgoers break down what's at stake in the 2016 election. Snapchat guru DJ Khaled preaches the keys to success.

33 min

Perils of Porn & Rachel Bloom's Big Year

Recovering addicts warn of porn's troubling side effects, and the "Crazy Ex-Girlfriend" star charts her journey from despair to a Golden Globe.

27 min

Ashton Kutcher & the App Economy

The actor-turned-mogul shares investing tips and joins Cindy McCain to shed light on human trafficking. Chelsea steps out as a dog walker for hire.

32 min

Dinner Party: Adventures in Parenting

Avowed non-parent Chelsea grills Kate Hudson and others about the appeal of raising kids and has her nails done by a gender-nonconforming 9-year-old.

38 min

Magic & GMOs with Lizzy Caplan, Bill Nye

The Science Guy weighs in on Chelsea's cryotherapy experiment and his new thinking on GMOs. "Masters of Sex" star Lizzy Caplan performs a magic trick.

36 min

Election Math & Megan Fox

MSNBC's Jacob Soboroff explains the fuss over superdelegates, and astrology maven Megan Fox tries to make sense of mixed signals in Chelsea's chart.

33 min

Warrior Dash & Will Arnett

Chelsea dives into a grueling mud race, Will Arnett puts a new spin on Trump's tweets, and "Daily Show" Hasan Minhaj talks Indian toilets.

35 min

Summits, Thruples & David Spade

Chelsea talks threesomes with the 'Do-Over' star, waits tables with her niece, and gets the inside scoop on Melissa Arnot's historic Everest feat.

31 min

The Case for Cannabis with Wiz Khalifa

The rapper joins California Lt. Governor Gavin Newsom to push for game-changing action on pot. Chelsea tries working out stoned with an MMA fighter.

33 min

Cocaine Kingpins & the Science of Sleep

Chelsea delves into the world of "Narcos" with star Wagner Moura and real-life DEA agent Javier Peña. Ariana Huffington warns of sleeping pill risks.

28 min

Ellen Page & Inspiring Role Models

The actress opens up about her LGBT travel show and the devastating toll of the Orlando shooting. Also featuring Florence Henderson, Von Miller.

32 min

Trump Mania & Kegel Exercises

Chelsea gives Mexican teens a whack at Donald Trump, while Keith Olbermann sizes up the candidate's psyche. Anna Faris and Allison Janney talk Kegels.

30 min

Paulson, Pelosi & Ayahuasca

"People v. O.J." star Sarah Paulson praises Marcia Clark. Nancy Pelosi calls for action on guns. Jason Biggs and Jenny Mollen share wild travel tales.

32 min

Biker Life & Michael Strahan

"Walking Dead" star Norman Reedus gives Chelsea a taste of motorcycle culture. Strahan talks flirting, good fortune and his new underwear line.

31 min

Devine, Bamford & Adult Coloring

Comedians Adam Devine and Maria Bamford talk stand-ups, psych wards and success. Chelsea tries a mindful coloring session with Metta World Peace.

34 min

Anna Kendrick & Social Media Snafus

The actress details a hair-raising outing in Hawaii. Comedian Jim Gaffigan responds to the backlash over his manicure tweet. Plus, modern dating tips.

34 min

Blake Shelton & Hillary's VP Options

The country star reveals how girlfriend Gwen Stefani upstaged him on his birthday. Former congressman Barney Frank shares his ideal Democratic ticket.

32 min

Tarzan, Mars & Aubrey Plaza

Alexander Skarsgård reveals his punishing 'Legend of Tarzan' diet, Aubrey Plaza fantasizes about freeing dolphins, and Chelsea studies the red planet.

31 min

Vicente Fox & All Things Mexico

Chelsea sips mezcal with actor Diego Luna, gets a history lesson from Eva Longoria and grills former Mexican president Fox on bullfighting and Trump.

Charlize Theron & Convention Fever

The 'Mad Max' star opens up about her nontraditional family and dream of stamping out HIV. Jacob Soboroff sizes up VP rumors ahead of the RNC and DNC.

Bill Maher & Dirty Water Polo Tricks

The 'Real Time' host rips into Donald Trump, a former top cop talks police militarization, and Olympian Tony Azevedo reveals racy water polo secrets.

LGBTQ Life with Jane Lynch & E.J. Johnson

The 'Glee' and '#RichKids' stars talk coming out, gay bars and evolving labels. A transgender woman and her partner share their transitioning story.

Bucking the Rules with Melissa McCarthy

The actress responds to 'Ghostbusters' skeptics and flouts fashion norms with her new clothing line. Zachary Quinto celebrates a 'Star Trek' first.

Brexit's Aftermath & Competitive Tickling

'Suicide Squad' star Adewale Akinnuoye-Agbaje and chef Gordon Ramsay break down Britain's predicament. 'Tickled' lifts the lid on a surreal world.

Trump's Other Reality Show

NeNe Leakes, Clay Aiken and fellow "Celebrity Apprentice" alums dissect the GOP nominee's appeal. Comedian Jim Jefferies poses with male strippers.

This Is My Home

Chelsea rents her house out to a Filipino family on Airbnb, Jay Leno relives a hairy crash, and actress Gillian Jacobs shares a terror of improv.

Tatiana Maslany Takes All the Good Parts

The 'Orphan Black' star shares the secret to playing clones. The Go-Go's reflect on 38 years of fun, fame and fistfights ahead of their farewell tour.

Dinner Party: The God Question

Reese Witherspoon, Common and friends of different faiths open up about their spiritual journeys. Chelsea gets a crash course in religious history.

Chelsea Does the DNC

Emotions run high as Chelsea crashes her first political convention and learns about a civil rights hero. With Jacob Soboroff and David Axelrod.

You Have a Speedo For Me?

Jason Biggs hops into the pool with the U.S. men's Olympic water polo team. The irrepressible Denis Leary riffs on his wild past and 27-year marriage.

A Prodigy in Our Midst

Chelsea's niece steps in as co-host, and Bryce Dallas Howard offers tips on growing up in a famous family. James Carville marvels at Trump's behavior.

Putting Compton Back on the Map

Mayor Aja Brown fights to rebuild a city plagued by turmoil. David Axelrod offers insights on Obama. Michael Kelly talks eerie 'House of Cards' plots.

Mission to Moscow

In the land of vodka, Chelsea braves a bracing spa ritual, tries rhythmic gymnastics with Maria Sharapova and probes the mystery of Russian men.

The Porn King of Japan

Chelsea gets sex tips from an adult film icon, talks history with 'Ben-Hur' star Jack Huston and urges the 'American Ninja Warrior' hosts to man up.

Zelda Williams Defies the Trolls

The actress reflects on her complex relationship with social media after the death of her father, Robin. Plus, Jon Favreau on Obama's writing habits.

Let's Go on My Tinder

Chelsea asks Tinder CEO Sean Rad for help with her profile and heads into the wilderness for survival school. With Eric André and Joel Kinnaman.

For You to Get This Hostile Is Weird

Sparks fly as Chelsea talks cats, fame and Obama with comedian Marc Maron and actress Natasha Lyonne. Plus, Olympic swimming champ Nathan Adrian.

We Have Influencers Here

Kate Upton and a crew of YouTube stars discuss the life-changing power of social media. Nasty Gal's Sophia Amoruso shares her wild success story.

How Could People Go Off on You?

Model Ashley Graham and country singer Jana Kramer bond over their brushes with public shaming. Plus, beauty pageant boot camp and comic Jimmy Carr.

It Felt Like Racist WrestleMania

Hasan Minhaj of "The Daily Show" recounts his hair-raising trip to the RNC, and the women of "Mr. Robot" celebrate their stereotype-defying roles.

That's MY Tight End

"New Girl" star Max Greenfield hails the joys of fantasy football, Noah Galloway discusses his post-"DWTS" breakup, and Jeff Ross roasts Ann Coulter.

Oh, This Isn't Funny Anymore

Comedian David Cross mourns the "quaint" early stages of Trump's campaign. Chelsea and "Sully" actor Aaron Eckhart talk phobias and hypnosis.

Dinner Party: The State of Politics

Chelsea invites a politically diverse group including W. Kamau Bell and S.E. Cupp to dissect the rise of Trump and the issues that divide Americans.

Flashbacks to the Good Old '80s

The kids from "Stranger Things" talk sudden fame and welcome a surprise visitor. Abigail Breslin slams an offensive tweet. Plus, comedian Bob Saget.

The Right, Fair Thing to Do

Oscar winner Patricia Arquette makes an urgent plea for equal pay, and Aisha Tyler rejects the toxic female relationships depicted on TV.

Sex in Space

Neil deGrasse Tyson explains the hazards of zero-gravity intimacy. Michael Sheen talks "Masters of Sex." Jenny Mollen obsesses over Jason Biggs's ex.

I Was a Ticking Time Bomb

Sarah Silverman opens up about a recent health scare and her fiery DNC remarks. Gloria Steinem talks politics and her Emmy-nominated Vice show.

My Story is an American Story

"OITNB" actress Diane Guerrero reflects on her parents' deportation. Mike Colter shares the symbolism behind Luke Cage's hoodie. With Craig Ferguson.

Fame Is Just Weird to Me

"Bridget Jones" star Renée Zellweger looks back on a life-changing phone call. Chris Geere recalls an awkward sex scene. Plus: Who is Alex Trebek?

Would You Buy Your Dad a Hooker?

Amy Schumer riffs on awkward family dynamics, dating life and pressure from fans. "Shark Tank" star Mark Cuban explains his change of heart on Trump.

Bareback Riding Skills

Chris Pratt and his "Magnificent Seven" posse talk feisty horses and behind-the-scenes bromance. Chelsea heads to the racetrack for jockey school.

I Was Naked on Broadway

Lea Michele's tales of stripping down take even Chelsea by surprise. NBA Hall of Famer Reggie Miller salutes Colin Kaepernick. With comic T.J. Miller.

Boys Are Told Not to Cry

"Girl on the Train" actor Edgar Ramírez rips harmful gender stereotypes. Jessica Alba shares the key to her Honest Company success. With Gavin Newsom.

When Ann Coulter Calls in Sick

Chelsea taps the conservative pundit's "body double" for a biting interview. Kristen Bell finds a cure for online gloom and doom. With Jacob Soboroff.

Climate Change Is Here and It's Real

Don Cheadle, Joshua Jackson, Ed Begley Jr. and the U.S. secretary of energy delve into the dangers we're facing and steps everyone can take to help.

I Love a Good Mean Joke

Rob Lowe dishes on his brutal Comedy Central roast and life as a Hollywood heartthrob. With comedians Nick Kroll, John Mulaney and Russell Peters.

It's Girl Empowerment

Krysten Ritter hails the cliché-crushing power of Jessica Jones. Rumer Willis pushes back on doctored photos. Plus, the inside story of "Amanda Knox."

Do You Know How to Use the Car?

Chelsea's bid to become a Lyft driver turns tense when she takes her mentor on a hair-raising ride. With Taylor Lautner and the Property Brothers.

So Let's Take a Test

Education Secretary John King quizzes Chelsea on geography and more. Glennon Doyle Melton calls out toxic messages to girls. Plus, Jennifer Connelly.

Dinner Party: These Strong Women

Chelsea sits down with Hilary Swank, Ava DuVernay, Connie Britton and the reigning Miss USA to talk ambition, sexuality, burning injustices and more.

That's When Madea Was Born

Tyler Perry reflects on a wild twist of fate, his foray into fatherhood and buying an Army base. With Cobie Smulders and Vice's Alyssa Mastromonaco.

I'm Here to Volunteer

Jason Biggs and Jenny Mollen go to work for Team Clinton. Journalist Jorge Ramos warns of a rising tide of hatred. With Isla Fisher and Thomas Lennon.

Whoa, I'm a Pop Star

Grammy winner Meghan Trainor dishes on her new beau, her creative process and more. Plus, Priyanka Chopra and transgender Senate hopeful Misty Snow.

I Feel Like I'm In a Fellini Film

Felicity Jones and Ron Howard talk "Inferno," awkward auditions and the closely guarded secrets of "Rogue One." Norah Jones hits the stage to perform.

It Tears You Down, and Builds You

Shannen Doherty offers a raw glimpse of how cancer has redefined her self-image, upended long relationships and changed her life -- for the better.

How Dark My Life Once Was

Nicole Richie opens up about her transformation from rebellious youth to poised mom and women's advocate. Plus, "Moonlight" star Trevante Rhodes.

So Fiercely Proud of My Mom

Chelsea Clinton speaks out about her mother's resilience, the high stakes in this election, and an "offensive" ploy by Trump. With Rose McGowan.

Please Take My Knickers Off

Stella and Mary McCartney talk fashion, royalty and sisterhood. Craig Ferguson offers a primer on Scotland. Plus, Colleen Ballinger and Kimbal Musk.

They Said It's a Man's Game

Comedy legend Carol Burnett shares the joys and hazards of hosting her own variety show in the 1960s. With Rob Corddry and ESPN's Jessica Mendoza.

Do Not Despair About Our Country

Chelsea sifts through the dizzying emotional and political fallout of the election with help from Sen. Barbara Boxer, Mary McCormack and Nikki Glaser.

Dinner Party: The Best Relationships

Sarah Jessica Parker, Morgan Spurlock, Trevor Noah and Julianna Margulies talk friends, parenting, work and the bonds that have shaped their lives.

Inside the Trump Tower Bubble

Jake Tapper weighs in on Donald Trump's shifting positions, Maria Shriver critiques Chelsea's interviewing style, and Matt LeBlanc talks "Top Gear."

You Secretly Hope You're Worthy

Emmy Rossum recounts a bold career move, Obama adviser Valerie Jarrett looks back on the president's big wins, and Flula explores the world of D&D.

You're Basically a Piece of Meat

Chelsea grills Milo Ventimiglia on the "Gilmore Girls" revival and his "This Is Us" physique. Kyra Sedgwick reflects on her 28-year marriage.

First Train to Tokyo

Chelsea heads to Japan to play drinking games with geishas, visit cat cafés and crying clinics, and interrogate the locals on dating, sex and more.

We Cannot Go Back to Sleep

Sally Field offers a defiant response to Trump's victory. Jacob Soboroff explains the recount process. Plus, Jason Biggs and a tribute to Mrs. Brady.

You Need to Be More Sexual

Jessica Chastain shares her grandmother's saucy advice, Chelsea makes a bet with Dale Earnhardt Jr., and Van Jones rebukes Democrats and Republicans.

Dinner Party: Going to Prison

Stars of "Orange Is the New Black" reflect on how the show has changed their lives -- and the world. Four women share their real-life prison stories.

Let's Talk Pipeline

Susan Sarandon breaks down the dramatic Dakota pipeline standoff and the #BankExit push. Gael García Bernal extols the pleasures of mezcal and Venice.

The Really Uncoordinated Superhero

Jennifer Aniston talks "Office Christmas Party" and her ideal superhero role. Fetty Wap explains his stance on guns. Chelsea gets high with her staff.

Both Naughty and Nice

Kate Hudson recalls a magical holiday, LA Mayor Eric Garcetti shares his plea to Donald Trump, and Cameron Dallas and friends talk social media fame.

We Got to See a Beacon of Light

Common looks back on Obama's impact, country star Maren Morris marvels at her wild year, and journalist Lauren Duca dissects lies by Trump.

Can You Tell I'm a Nightmare?

In the season finale, Oscar winner Jennifer Lawrence gets punchy, Chris Hardwick talks zombies, and Chelsea revisits favorite moments from the show.