Kristen Wiig joins the SNL five-timers club as Ryan Gosling, Paul Rudd and other A-list stars make SURPRISE cameos during latest episode

Kristen Wiig officially joined SNL‘s five-timers club as she took on hosting duties for the fifth time during the latest episode of the popular sketch comedy series. 

The Bridesmaids actress, 50 – who recently reprised her SNL role of the Target lady in a humorous ad for the superstore retailer – was also joined by British songstress and musical guest, Raye, 26. 

The show kicked off with a star-studded monologue as several celebrities made surprise cameos to help celebrate Wiig’s milestone – including Ryan Gosling, Paul Rudd and Matt Damon.  

At the beginning, Kristen stepped out onto the stage and was welcomed with loud cheers and applause from the live audience. 

She dazzled in a pair of sparkling, black trousers as well as a black, strapless corset top before addressing the excited crowed. 

The star gushed that she was ‘happy to be back’ and thrilled to be taking on hosting duties for the fifth time – which officially landed her into the five-timers club. Before continuing, Wiig took time to send a special greeting to the band directly behind her.

As she began speaking once again, Kristen was suddenly interrupted by Paul Rudd who stood up in the audience while sporting a five-timers jacket. 

‘This is exciting. It’s so exciting. Aren’t you excited?’ the actor exclaimed. ‘Tonight you’re getting your five-timers jacket. Look at mine, huh?’ 

Rudd began to flaunt his velvet jacket and then expressed his desire to take part in one of the sketches during the night. 

However, Kristen revealed, ‘Oh, sorry. I don’t think we’re doing one of those,’ causing Paul to sit down with a look of devastation. 

The Bridesmaids actress then began to share her excitement about getting her five-timers jacket when former SNL writer, Paula Bell, also stood up in the audience. 

She told Wiig, ‘I think it’s so sweet that you’re so excited about getting a five timers jacket. You know, they basically hand those out to everybody like free…’ But Kristen argued that someone needs to host five times to get the jacket. 

Matt Damon then made a surprise cameo, and he expressed, ‘Hi, Kristen. Well, first off, big fan. I just want you to know I grew up watching you on SNL.’ The star sent the actor a confused look since they are only three years apart. 

She pointed out that Damon only has hosted twice and asked how he had a five-timers jacket. 

He explained that Lorne Michaels told him that ‘the first time I hosted was so good, it counted for three. And then, second time, not quite as good, that only counted for two. But by my math, that’s five, baby.’ 

‘Well, that doesn’t really seem fair,’ Kristen said. ‘I mean, I’ve hosted five times. I earned this, right? Doesn’t this jacket have any meaning anymore?’ 

Suddenly, the camera cut to Lorne, as well as Jon Hamm, Fred Armisen, Martin Short and Will Forte – who were also sporting five-timers jacket. 

However, Wiig pointed out that they haven’t hosted five times. ‘Guys, what is going on here? I was really excited about being in the five-timers club, but now it seems like it’s not even that special.’ 

Matt approached her and offered his jacket, but she told him to keep it. He them mentioned how he had appeared in cameos on SNL and was given another jacket in front of Kristen. 

She was then joined by all the celebrities that had made cameos during the monologue as they sang her a song to celebrate the big milestone that she had made. 

However, Ryan Gosling suddenly appeared, causing the audience to erupt into excited screams and applause. The Barbie actor also was seen wearing a five-timers jacket. 

To conclude the monologue, the large group presented the Palm Royale actress her very own five-timers jacket as she was inducted into the club. 

Kristen also had the chance to show off her comedic skills by appearing in various sketches throughout the night. 

The first skit showed the former SNL cast member taking on the role of a Nina who was at a dinner party with her boyfriend and his friends. 

After enjoying a yummy meal, one of the pals – played by Andrew Dismukes – pulled out a board game called Ticket To Ride. 

The guests expressed excitement to play the game except Wiig – who simply said, ‘Oh wow. No. No. Sorry.’ She further explained that she doesn’t play board games.

Her boyfriend chimed in to say, ‘Oh, yeah. Sorry, y’all. Nina doesn’t play board games. She’s kind of freaked out by them.’ 

Kristen then told the guests that she wasn’t necessarily ‘afraid’ of board games, she was just scared of ‘getting Jumanjied’ – referencing to the 1995 film with Robin Williams. 

She added, ‘I just want to be cautious playing games. I don’t know. Lest it should Jumanji me.’ 

Other guests told her that Jumanji was just a movie about a fictional game that doesn’t exist in real life and added she would not be ‘Jumanjied.’ 

‘I know I’m not getting Jumanjied because I will not put myself in a position to be Jumanjied,’ Kristen adamantly stated. 

Dismukes said in an annoyed tone, ‘What even is Jumanji to you, lady? Because it sounds like you think Jumanji is going into Jumanji, but in Jumanji, Jumanji comes out. The kids don’t go into Jumanji, Jumanji comes out of Jumanji.’

Wiig said, ‘Jumanji is a series of jungle emergencies. That sir, is Jumanji, and we are not prepared for that. We have no medicines. We have no rope!’ 

However, Wiig was told that if they were Jumanjied, they wouldn’t get trapped in a jungle because the board game they were about to play was simply about trains. 

Dismukes opened the game and fog began to surround them. The group was then transported to a railroad and were greeted by a train conductor – played by Will Forte. 

He told Kristen that she was ‘free’ to leave since she previously said she did not want to be Jumanjied. 

‘Yes! I knew it. I’m free,’ she said, jumping out of her seat. Kristen then told her boyfriend, ‘I don’t think this is going to work out because it seems like you and all your friends are going to die.’ 

She ran off and Forte told everyone else, ‘Aww, you lost your girl. That’s too bad. But, hey, just remember, if you lose the game, you die in real life. Hope that helps. All aboard!’ 

The next sketch was pre-recorded and was a movie trailer for a horror film centered around Pilates. 

Two pals, played by Chloe Fineman and Molly Kearney, entered a dark room at the beginning and soon discovered – to their horror – that it was a Pilates class. Wiig took on the role of the instructor. 

The clip then cut to Sarah Sherman warning Fineman about the class. ‘It’s not what you think it’ll be. It’s so hard, but it’s also so boring.’ 

The trailer showed some of the complex exercise equipment but Chloe said, ‘It can’t be that bad.’ Sarah replied, ‘You don’t understand. Time is different there.’ 

The trailer jumped to Chloe struggling in the class and asked Kristen, ‘How long has it been? Four hours?’ Wiig then told her after glancing at her watch, ‘It’s been 11 seconds.’ 

The scene with Fineman and Sherman returned, and Chloe asked who the women were in the class. 

Sarah explained, ‘The vibe is bad. Most of the women are ex-dancers or first-time moms.’ She then said explained that Kaia Gerber also showed up ‘sometimes.’ 

The daughter of Cindy Crawford also made a surprise cameo as she enjoyed the Pilates class. 

The trailer ended with Chloe in the class and she asked her friend to leave. However, she had become one of the women who love the class. 

The third sketch of the night took place around the 1950s-1960s with Jon Hamm and Bowen Yang. Jon portrayed a lawyer and Yang took on the role of his client. 

Heidi Gardner played the character of Hamm’s secretary named Trudy who is notorious for finishing his sentences. 

But Jon explained that she was only right a portion of the time, so he hired a second secretary named Tootie – played by Kristen. 

She also began to finish his sentences, including one where she picked up his son from school. However, Hamm pointed out that he does not have a son. 

The Mad Men alum and Bowen then asked for drinks to be made, and both Trudy and Tootie sauntered to the bar to make a ‘bourbon on the racks.’ 

After both Hamm and Yang went into another office, Kenan Thompson appeared to deliver lunch. However, he left quickly after Tootie tried to finish all his sentences. 

Jon reappeared with Bowen so he could retrieve his lunch. At one point, Tootie stumbled and fell through the wooden desk, loosing her skirt in the process. 

Trudy also took a tumble and ‘fell right through the office globe’ while loosing her shirt in the accident. ‘And her top got sucked into space,’ Yang said. 

Hamm then asked Tootie if she was okay after falling, and he pronounced his love for her. 

Bowen walked up to Trudy, who had the office globe covered her entire head. She assumed that he was about to pronounce his love for her and she asked him to ‘dip’ her. 

However, she fell backwards and into the wall, causing the globe to humorously fly off her head. 

In conclusion and with a smile on his face, Yang said, ‘Well, ain’t love a catch. Now if you’ll excuse me, I’m going to have another bourbon on the racks.’ 

Another skit took place at a retirement party for a man named Jerry – played by Kenan Thompson. His coworkers were seen giving special speeches including Bowen, who recounted a story about Jerry. 

He recalled bringing his service chinchilla to work named Pebbles but tragically recounted, ‘Somehow pebbles got stuck in the industrial fan and was tragically killed to death.’ 

Bowen said that Jerry helped find the remaining body parts and put them in a Starbucks cup and returned the mug to him. 

The office musical improv troop – which comprised of Paul Rudd, Punkie Johnson and Chloe Fineman – then stepped up to say a few words. However, they revealed that they had been asked to not perform. 

Fred Armisen also wanted to give a speech and expressed how much he would miss Jerry, but ended up revealing he did something ‘sacred’ with another office employee. 

Wiig suddenly appeared, slowly making her way to the host who was holding a microphone. She had an oxygen tank next to her and said that Jerry stole from the company. 

He immediately denied it and Kristen quickly added, ‘He’s been stealing our hearts.’ She then said, ‘Jerry assaulted me.’ After a shocked moment passed, she quickly added, ‘With guidance and information.’ 

‘He was a great mentor. Never be alone in a room with Jerry,’ Wiig said in warning. But added, ‘Because he’ll make you laugh so hard you can’t breathe. He kissed me once on the mouth.’ 

The host took the microphone away from her and Matt Damon appeared and introduced himself as a Hollywood actor and found Jerry while researching for a role.

‘The character was a sex addict, a peeping Tom character with a major armpit fetish. Naturally, that led me to Jerry,’ Damon said, causing Kenan to reply, ‘Hey, man. My family is here!’ 

Will Forte also made a speech and wore a blonde wig and brown shades as he took the microphone. He played the step-nephew of the event coordinator. 

He went into detail about death and then at the very end, admitted that he had murdered Bowen’s chinchilla. 

The next sketch took place at an amusement park with Wiig portraying a mom, James Austin Johnson played a dad and Andrew Dismukes playing their son. 

While waiting on a go kart ride, Andrew couldn’t hide his excitement for the ride until James said, ‘Enjoy the go karts, son. Let’s all have fun on the go karts because after the go karts, your mother and I have something terrible to tell you.’ 

He asked what it was, but Kristen cut in to tell Andrew to enjoy the ride ‘and then after that, your father and I will tell you something very bad.’ 

But Dismukes kept asking his parents to tell him the ‘bad’ thing, but both Kristen and James said they would wait to do so. 

They then asked their son if he wanted them to tell him after going on the next ride. ‘You know what, we shouldn’t even be asking him something like that,’ Wiig said. 

James agreed and suddenly, the camera panned to show their daughter Ashley had also been sitting on the go kart ride the whole time. James then asked her what she wanted to do since it was her birthday.

She also explained that she wanted to hear the ‘bad thing’ right away, but the parents refused to tell. 

Kristen said, ‘Kids, we’re going to just play telling you the bad thing by ear, okay? So the rest of the day, just be ready. At some point, we’re going to drop it on you, okay?’ 

Their dad then explained that Sheila should be there when they tell their kids the ‘bad thing.’ However, the children kept asking who Sheila was. ‘She’s part of the bad thing,’ Wiig answered. 

Finally, Andrew stated, ‘Okay. Look, enough. Mom, dad, please, just whatever the bad thing is, tell us. We can handle it.’ 

Kristen gave in and said, ‘Okay. Fine. Before we tell you, I want you kids to know your father and I love you, and we always will.’ 

James added, ‘That’s right. And no matter what happens, we’re still mom and dad. That’s never gonna change.’ 

However, just as they started to tell the ‘bad thing,’ the ride started – which ended the sketch.   

The last skit in the latest episode was a PBS episode of the show called Sonic Pioneers – hosted by Ego Nwodim. 

She looked, ‘at one of the most influential French television programs in the 1970s, the music variety show La Maison Du Bang. It had been hosted by a ‘real-life married couple’ named Jules and Camille – played by Bowen Yang and Chloe Fineman. 

Ego explained that they were known for their catchy theme song and in a ‘throwback clip,’ both Yang and Fineman sang and danced to an upbeat tune. 

One of the artists featured on the show included ‘Tipi Tornade, the dancing tornado, with her hit, Help! You’re Making Me Dance.’

Wiig took on the role of Tipi, and wearing a colorful ensemble, she showed off a few humorous dance moves while singing lyrics. 

Other artists were introduced such as Coco DuBois who was ‘a heavy smoker’ and ‘two white guys from Toulouse’ with ‘their hit La Papillon.’

Kristen jumped into their dance number and Ego explained, ‘Yep, there’s Tipi Tornade again, who became a regular on the show because she was actively squatting in the studio.’ 

Ego then said, ‘The show wasn’t just about music. It also featured fun variety acts like the popular mime, Spirou. Spirou had never done television and accidentally stood too close to the camera.’ 

The host explained that the show was eventually cancelled when Jules and Camille divorced over ‘irreconcilable murder.’ 

Just as the segment ended, Kristen suddenly appeared next to Ego and began doing a dance number from her hit track. 

British singer, Raye, was the musical guest for the latest episode and the first song she performed on stage was Escapism – which is found on her debut album titled My 21st Century Blues. 

Last month in March, the album notably won Album of the Year at the 2024 BRIT Awards. 

She showcased her impressive vocal skills while wearing a figure-hugging black dress as she took to the stage. 

The star later performed the tracks Worth It as well as Let There Be Light while sporting the same ensemble from earlier in the night.