Late-Night Lately: Fallon in Puerto Rico, Kimmel Pitches YouTube, Presidential Plans

5:15 AM 1/19/2019

by THR staff

The Hollywood Reporter's Late-Night Lately rounds up the best sketches and guests with a look at what's to come next week.

LATE NIGHT LATELY-Jimmy Fallon-Jimmy Kimmel-Kirsten Gillibrand-Publicity Stills-Split-H 2019
Andrew Lipovsky/NBC; ABC/Randy Holmes; Scott Kowalchyk/CBS

The Hollywood Reporter's Late-Night Lately is a one-stop shop for all of the most memorable moments of late-night TV, coming to you each Saturday morning to ease you into your weekend.

So fill up your coffee, set your DVR for the week and sit back. Below are a few of the week's best, funniest and strangest late-night moments you can't afford to miss.

This week: Jimmy Fallon and his show visit Puerto Rico with Lin-Manuel Miranda, Jimmy Kimmel tried to pitch video ideas to YouTube after the site banned any videos promoting dangerous behavior, and Sen. Kirsten Gillibrand announced her intention to run for president in 2020 on The Late Show. Elsewhere, Comedy Central combined The Daily Show and Drunk History to reenact Trump's speech about the Civil War. 

— Compiled by Jennifer Konerman  

  • Fallon, Lin-Manuel Miranda Perform 'Hamilton' Songs in Puerto Rico

    Jimmy Fallon visited Puerto Rico to raise relief money for artists affected by the hurricane in 2017, and he documented his experience on Tuesday's Tonight Show. 

    First, Questlove and Tariq "Black Thought" Trotter quizzed Fallon on his knowledge of Puerto Rico. After he surprised them with his knowledge, he took off to the island where Fallon visited Lin-Manuel Miranda on set at the opening of Hamilton, in which Fallon donned full costume to perform "The Story of Tonight" from the Broadway hit — with updated lyrics for The Tonight Show's open. 

    Fallon also took to the streets with Questlove, Black Thought and Puerto Rican singer Bad Bunny to dance to the musician's hit "MIA." They were joined by a group of local residents and musicians waving Puerto Rican flags and playing instruments.

    Miranda and Fallon sat down on the Hamilton stage to speak about the performances in Puerto Rico. "There's a song in this show called 'Hurricane' and I could barely get through it last night," Miranda responded: "Never in a million years would I imagine it would resonate in this way," he said of writing the song years ago.

    The interview focused on the importance of supporting Puerto Rico, specifically by taking advantage of small businesses. "We're trying to promote tourism and people coming and visiting our island — not just sort of going to the hotels," said Miranda.

    He also shared that the trip was the first time he has brought his children to the island and that the actor's four-year-old son saw his full performance in Hamilton for the first time during the trip. "I prepped him. I was like, 'Everything Daddy does on that stage is pretend. Kissing that lady, getting shot by that guy. That's all pretend,'" he said. "We sort of talked through it, but he was really proud."

    Chef Jose Andres also joined Fallon to discuss Puerto Rico's food and his charity, World Central Kitchen. The episode concluded with a performance of "En Mi Viejo San Juan" by Jose Feliciano and Ozuna. 

  • Jimmy Kimmel Pitches YouTube Challenge Ideas

    On Thursday's Jimmy Kimmel Live, the prank-loving host addressed YouTube's recent announcement that they are banning videos of users engaging in dangerous content in the wake of the Bird Box challenge, in which people often try relatively dangerous activities while blindfolded.

    YouTube recently updated its policies to clearly state that challenges that have the potential to cause death or physical injury "have no place on YouTube."

    "I have to say, as someone who loves a good prank and likes to do them, I think it's sad that a few bad apples had to ruin the fun of eating poisonous detergent packets for everyone," Kimmel joked. 

    The host then questioned what YouTube considers to be dangerous, and he even went over to their office to run some ideas by them. During the meeting, Kimmel said that he was concerned that some of the content they film for the late-night show may be considered dangerous by YouTube.

    "We trust what you do. That's a different situation," said the executive.

    "So I can do anything?" he asked.

    She responded, "Well, I wouldn't say anything."

    Kimmel asked if he could run a few ideas by her to make sure they could be included on the platform, including the "I bet you can't eat all the knives" challenge, "setting my brother on fire" challenge, "Dad, I boiled the toaster" challenge, "jump the zoo fence" challenge and "let's make friends on Craigslist" challenge.

  • Kirsten Gillibrand Takes First Steps Toward Presidential Run

    Sen. Kirsten Gillibrand on Tuesday announced she was filing an exploratory bid to run for president in 2020 during an appearance on The Late Show. 

    When asked why she wants to be president, Gillibrand responded, "As a young mom, I’m going to fight for other people’s kids as hard as I’d fight for my own, which is why I believe health care should be a right, not a privilege; it’s why I believe we should have better public schools for our kids because it shouldn’t matter what block you grew up on; and I believe that anybody who wants to work hard enough should be able to get whatever job training they need to earn their way into the middle class." She added, "I know that I have the compassion, the courage and the fearless determination to get that done."

    After Colbert asked the senator to clarify what forming an exploratory campaign means, she said that it was an "important first step" toward running for president but affirmed, "I am going to run."

    When asked what she would do on her first day in office, Gillibrand replied, "The first thing I would do is restore what's been lost, the integrity and the compassion of this country, I would bring people together to start getting things done."

    The two-term Democratic senator from New York joins other Democrats who have entered the race against President Donald Trump in 2020 in recent weeks, including Hawaii U.S. Rep. Tulsi Gabbard, Massachusetts Sen. Elizabeth Warren and former federal housing secretary Julian Castro.

  • Trump's Civil War Rant Gets 'Drunk History' Treatment

    Drunk History host Derek Waters teamed up with The Daily Show's "World's Fakest News Team" to reenact Donald Trump's version of the Civil War that the president related at an Ohio rally in October.

    The clip opened with Waters raising his glass to Trump, who appeared through TV clips as the show's "narrator," and a voiceover from Trump's speech played as Waters took on the role of Abraham Lincoln to reenact Trump's storytelling. Characters in the scene, played by Daily Show correspondents, paused when Trump slurred his words and butchered the pronunciation of "imagining." 

    Trump's voiceover then transitioned his story to a battle in the Civil War that was led by General Robert E. Lee. He went on about Lee's drinking problem and "winning," as Grant punched out other soldiers and kept drinking. "And you know the story. They said to Lincoln, 'You can’t use him anymore. He's an alcoholic.' And Lincoln said, 'I don’t care if he's an alcoholic. Frankly, give me six to seven more just like him.'"

    The clip went on to pan across the other correspondents as they shook their heads at Grant. 

  • Seth Meyers Debuts "What Is Brexit?" Ad

    Seth Meyers shared a fake commercial that explained Brexit on Wednesday's Late Night.

    "Brexit has been in the news quite a lot lately and there's still quite a few people, specifically Americans, who don't fully understand it," began the host. 

    The fake commercial opened with three women celebrating a friend's birthday. When one asked about Brexit, one woman responded: "I'm pretty sure Brexit is the most important meal of the day." 

    "Not quite. 'Brexit' is just a term for Britain's recent decision to leave the European Union," the third friend said. "Some British people want to control their own trade agreements instead of having them controlled by a larger unorganized body, while other British people think it's better to be part of a group of bodies that all work together."

    "Like an orgy," added the woman celebrating her birthday. They continued to explain the concept, now setting off debates in Europe. The fake commercial concluded with a voiceover that stated, "America, be glad we got out of Britain when we did."

  • Late-Night Lineup: January 20-26

    Monday, January 21
    Jimmy Kimmel Live!: On the same night that host Kimmel appears on Bravo's Watch What Happens Live, he also plans to "salute" the midpoint of Trump's term in office with the "Jimmy Kimmel Live Intermission Accomplished: A Halftime Tribute to Trump."

    The Late Show With Stephen Colbert: Rep. Alexandria Ocasio-Cortez continues Colbert's line of high-profile political guests. 

    Tuesday, January 22
    Conan: Team Coco returns on TBS with a new format with the man who coined the Coco nickname himself: Tom Hanks.