10 of the Most Iconic and Awkwardly Hilarious Moments in Emmy History — in 30 Photos

From unexpected kisses to spinning platforms and onstage proposals, the Emmys have seen it all. These 10 hilariously awkward moments — captured in 30 unforgettable photos — show exactly why live TV never fails to surprise.

Every year, the Emmys promise glitz, glamour, and gold statues. But let's be honest — it's the unexpected, unscripted, and utterly unhinged moments that keep us coming back for more.

In this roundup, we're reliving 10 of the most iconic and awkwardly hilarious Emmy moments told through 30 unforgettable photos that prove one thing — when it comes to live television, anything can happen... and usually does.

When Julia Louis-Dreyfus Locked Lips with Bryan Cranston

It was the kiss no one saw coming, and yet it stole the entire night. At the 2014 Emmys, Louis-Dreyfus had just been named Outstanding Lead Actress in a Comedy Series for her razor-sharp performance in "Veep."

But as she made her way to the stage, viewers were left gasping when Cranston intercepted her path and planted a full, passionate kiss on her. The moment was one for the books. But as it turns out, the sultry smooch was partly planned.

In the days leading up to the show, the two actors, who once shared screen time as a couple on "Seinfeld," joked about the idea during their rehearsal as co-presenters.

With their spouses' blessing and a shared flair for comic timing, they made a pact — if she won, they'd go for it. It was risky, unexpected, and comedic gold.

Donald Trump and Megan Mullally's Surreal 'Green Acres' Duet

Before the presidency. Before the politics. There was Emmy Idol. In a 2005 segment inspired by "American Idol" mania, the Emmys included a gimmicky musical performance challenge. And nothing — truly nothing — prepared viewers for what came next.

Mullally, fully in character as her "Will & Grace" alter ego, was tasked with belting out the "Green Acres" theme song. But her duet partner? None other than Trump, dressed in overalls and clutching a pitchfork.

The surreal visual — the current president singing on national TV in farm wear — became one of the evening's most jaw-dropping moments.

When Matthew Perry and Doris Roberts Surprised Everyone with a Kiss

It was the kiss that came out of nowhere and left the audience stunned. At the 2003 Emmys, Perry and Roberts shocked the audience when they shared a spontaneous kiss onstage.

The unexpected moment quickly became one of the ceremony's most buzzed-about highlights. Later, Roberts reflected on the now-iconic moment during an appearance on "The Ellen DeGeneres Show," teasing that he was a "good kisser."

Glenn Weiss Bringing the House Down with an Onstage Proposal

Tears. Gasps. And a live proposal in front of Hollywood's biggest stars. During the 70th Primetime Emmy Awards in 2018, director Weiss took the stage to accept his award for Outstanding Directing for a Variety Special.

But after a touching tribute to his late mother, the speech took a romantic twist. Turning his attention to his partner, Jan Svendsen, in the audience, Weiss stunned the room by inviting her onstage and proposing on the spot.

The crowd erupted in cheers as Svendsen, visibly shaken and overwhelmed, said yes. It was a moment of authentic love rarely seen at an awards show, capped off with a standing ovation that brought the house down.

When Alexander Skarsgård Won, and Nicole Kidman Congratulated Him Like Any (TV) Wife Would

Things got steamy onstage in 2017, but not in the way anyone expected. At the 69th Emmys, Skarsgård took home a win for his chilling portrayal in "Big Little Lies."

But what grabbed even more attention? The congratulatory kiss from his co-star — and TV wife — Kidman.

As Skarsgård approached the stage, Kidman rose, smiled, and congratulated him with a quick kiss on the lips. Cameras caught it, everybody saw it, and the actress couldn't live it down.

Appearing later on "The Graham Norton Show," Norton teased Kidman about the moment, to which she responded, "You are so provocative."

Jennifer Aniston and Jimmy Kimmel Play with Fire – Literally

At the 72nd Primetime Emmys in 2020, host Kimmel tried to keep things interesting in an empty Staples Center. Enter Aniston, who joined him to present the Outstanding Lead Actress in a Comedy Series award, and ended up fighting flames.

In a bizarrely elaborate attempt to sanitize the winner's envelope, Kimmel sprayed it with disinfectant, then lit it on fire. Aniston, poised with a fire extinguisher, was tasked with putting out the flames. The result? Comedic chaos that was perfectly in sync with the pandemic weirdness of the year.

Alan Alda Cartwheeling His Way into Emmy History

The year was 1979, and Alda didn't just walk up to collect his Emmy. He cartwheeled. After winning the Writing in a Comedy Series award, Alda — already a multiple Emmy recipient — bounded toward the stage at the Pasadena Civic Auditorium and surprised everyone with a mid-aisle acrobatic display.

Presenters Penny Marshall and Cindy Williams looked on, stunned and amused. Alda would later say he was just "really, really happy." Sometimes, joy literally flips you upside down.

When Helen Mirren Took the Stage and Avoided Taking a Tumble

In 2006, Mirren claimed the Emmy for Outstanding Lead Actress in a Miniseries or Movie and successfully avoided tripping on her way to the podium.

Ever the consummate Brit, she joked to the crowd, "My great triumph is not falling [expletive] as I came up those stairs. If you saw the shoes I've got on, you'd understand."

She ended her speech with a cheeky flourish, declaring she would "take [her] bloody shoes off," earning huge laughs and solidifying her place as an Emmy icon — heels or not.

Sofía Vergara Spinning Through an Awkward Emmy Gag

At the 66th Primetime Emmys in 2014, Sofía Vergara was asked to help introduce TV Academy Chairman Bruce Rosenblum.

But instead of standing still, producers had her slowly rotate on a revolving pedestal as a cheeky visual gag while Rosenblum gave a speech about diversity.

Critics blasted the segment as sexist and demeaning, but Vergara didn't agree. Defending the skit backstage, she insisted it proved a woman could be "hot" and "funny."

Jon Hamm Climbing His Way to an Emmy Win

After eight nominations, the Emmy for Hamm was long overdue. But when he finally won in 2015, he didn't take the stairs. Instead, the "Mad Men" star literally crawled onto the stage, straddling the platform in a moment that was equal parts awkward and hilarious.

Backstage, he admitted the crowd's wild reaction left him stunned. The applause didn't register until he looked back and saw everyone on their feet, leaving him completely mortified.

Whether it's unscripted smooches, offbeat musical numbers, or unexpected onstage proposals, the Emmys have proven time and again that anything can happen once the cameras start rolling.