Despite his natural talent for making people laugh, it was sport that seemed to be the logical career step for Will. He graduated with a bachelor’s degree in Sports Information in 1990, and he even earned an internship in the sports department at a local television station. However, that internship proved to be a negative experience – and it would fuel his decision not to pursue a career in broadcasting.

Instead of a sports broadcasting career, he worked on a number of jobs, including stints as a hotel valet, with a second-day disaster after he drove a van under a low-lying beam, knocking the baggage rack off the top of the van. Another job saw him working as a teller at Wells Fargo, but that didn’t go so well after coming up $350 and $280 short in the first two days – as a result of incompetence, not theft. A year of this saw him disillusioned, and his mother encouraged him to pursue something he loved. As a Christmas present he was given nine weeks of acting classes by his mother. It was a gift that would change his life.

He told NewsOK: ‘I absolutely loved it. And kind of at the same time on my list of things to do in life was to try to do one night of stand-up comedy. … I’d always been able to make my friends laugh and then I was starting to make strangers laugh. And then I thought, “Oh, maybe I can do this.”’ He would perform small comedy sets in Irvine, but his surreal brand of comedy wasn’t quite to the taste of the fairly conservative-minded town. He explained to Premiere: ‘There’s an improv down in Irvine, two minutes from my house. I would go and I would sit in the back of the room on their open mike nights and gauge. “I think I’m as funny as that person.” But I didn’t have the guts enough to get up there. But I did a stand-up comedy workshop in an Irvine Valley College extension course catalogue. I thought, “Oh my God, this is perfect.” It will force me to have to get up and perform. The six weeks ended in a performance at the old Golden Bear down in Huntington Beach, which I think is torn down. That was the kindest audience ever, people in the class and family and friends, I thought: “Oh my gosh this is fantastic. I’m a natural.” So my first time in front of a real audience was a place called The Barn, in Tustin. It wasn’t promising at all. The TV blaring in the corner, guys playing pool while you’re standing up there with a microphone. I got so nervous that all of the moisture left my mouth, so I couldn’t keep my upper lip from sticking to my teeth. And I kept going “gaack”. I sped through my material, then “Thanks for coming. I’m Will Ferrell” – just flop sweat, the worst. I drove home and went, “Mom, how do you think it went?” She went “I think you did really good. You have a nice presence, but you have a bad tic.” And I said, “Mom, that’s because all the moisture left my mouth!”’

In 1991, he decided to move to LA. As for many others, it was initially a struggle. He went to a scene study, where he was met with ruthless feedback – being told that, not to be mean, but he wasn’t really any good. He recalled to Backstage: ‘I remember going to one of those casting workshops, where you pay 50 bucks and go off and work on scenes. I came back and they evaluated me, and the guy was like, “Conservatively speaking, you need three more years of work, probably working at our workshops.” I was like, “Uh-huh, OK.” Not to say that he was wrong and I was really good, but it just felt creepy and weird. Also, in the limited amount of commercial auditions I used to do, I swear every time I went in, the person in front of me would come out laughing with the casting director. They’d be hugging each other: “Bye, Bob! Great to see you! Say hi to the wife!” Then they’d be like: “Next! Phil Ferrell!” “Uh, it’s Will, actually.” “Whatever.”’

However, Will believed that you have to go with your instincts – something that is never more true than when working in comedy – with Ferrell reasoning that your gut hope is all you have in comedy, and you forge ahead hoping against hope that people find you funny too. It was during advanced acting classes he discovered that he enjoyed improv comedy. Soon, he began to hone his talent for impersonation – including Hall of Fame baseball announcer Harry Caray – a character he would reprise on Saturday Night Live (SNL). He also began to create original characters with comedian Chris Kattan – a future Groundling and SNL member. They created the Butabi Brothers – two buffoons who go to nightclubs to unsuccessfully pick up women. Sensing momentum in the art of making people laugh, he then decided to ask his dad for advice on giving this ‘comedy thing a try’.

Will had seen how a career in the arts had broken up his family, with his dad’s busy working schedule seeing him on the road for many months. But his dad surprisingly didn’t talk him out of it – instead passing on sage advice that was gained from years of watching talented people never quite earn the success they deserved. He told his son, ‘If it wasn’t based on luck, I wouldn’t worry about it, because you have talent. Just know that there’s a lot of luck involved and if you eventually decide to do something else, don’t treat it as a failure. Just know it’s one-in-a-million.’ His father’s advice, according to Will, took the pressure off, and he treated his attempt at becoming a comedian as just a game. With his confidence flourishing, he would even take to the stage and attempt stand-up once again, an intimidating battlefield that leaves no room for the weak and has spat out many a would-be comic.

‘I wasn’t a very good joke writer, but my strength was in setups, premises, and then going into observational humour,’ he said (Port Magazine, 15.2.2013). ‘With stand-up, you’re given five minutes, and I’d get maybe two chunks out before my time was up.’ His early routine would find him humming the Star Trek routine, a quirky set-up that would actually find an audience clapping. He revealed to AintItCoolNews.com: ‘Well, I didn’t really do that much stand-up. I tried a little, for like a year and a half and maybe did it thirty times. Then I heard about the Groundlings in Los Angeles and I, all at the same time, took classes there all the while doing stand-up and taking acting classes. Then the more I got into the Groundlings programme, stand-up kind of fell by the wayside because it’s such a solitary pursuit. It’s really exhilarating when it’s just you and it’s going great, and it’s like the worst when it’s going bad. Doing sketch and improv with other people is just so much fun. Plus if you fail, at least you’re up there with someone. So I had more training in the sketch world to begin with.’

Bolstered by the audience reaction, he tried out, as stated above, for the Groundlings in 1994. The Californian improv and sketch comedy troupe called the Groundlings was founded in 1974. Its name is taken from a line in Hamlet – ‘to split the ears of the groundlings, who for the most part, are capable of nothing but inexplicable dumb-shows and noise’. On its website it states, ‘The Groundlings is an improvisation and sketch comedy theatre that has been entertaining LA audiences for over 36 years. We’re a non-profit organisation founded by Gary Austin in 1974. A “Groundling” is one of the 30 company members who write and perform in the theatre’s shows and teach classes at the Groundlings School. Our school has been the foremost comedy training ground in Hollywood and the springboard for countless careers. … Our alumni include Will Ferrell, Kristen Wiig, Phil Hartman, Lisa Kudrow, Paul Reubens, Cheryl Hines, Jon Lovitz, Laraine Newman, Will Forte, Maya Rudolph, Michael McDonald, Kathy Griffin, Phil LaMarr, Cheri Oteri, Chris Kattan, Julia Sweeney, Chris Parnell, Ana Gasteyer and Rachael Harris … just to name nineteen.’

Describing how the Groundlings came to be, Austin told The Hollywood Reporter: ‘I was an actor in The Committee in San Francisco. I moved down here, and I was broke. I went to the Hollywood Unemployment Office, where I used to stand in line with Penny Marshall, and I got to the window and the woman said, “Due to a technicality, you are no longer eligible.” I panicked and called Howard Storm, who was teaching at the Cellar Theater on Vermont. That was a Thursday. I started teaching on Monday night. Fred Roos, who was the head of feature casting at MGM, gave me 75 names and phone numbers. Tracy Newman, who was my friend, helped me round up a bunch of people from the Comedy Store. So my first night teaching, I had 21 students. I taught for one year, all kinds of people came through. It became kind of a magnet. … We improvised scenes and monologues, and we did scenes from Pinter and Molière and so on. And after a year of doing that, I said, “Let’s create a company.” We created the Groundlings. I thought of the name. It’s from Hamlet’s speech to the players.’

Will was accepted into the comedy group, and that was where he discovered that, while there were wittier people with faster improv skills, one thing that could be guaranteed from Will was that he wouldn’t hold back. It would be a trademark Ferrell move – the idea that you give everything to a character. He said in a past interview with Esquire Magazine: ‘It was just funnier to me, and it played funnier, when instead of just yelling at someone in a scene, you’re yelling to the point where you’re losing your voice – that one extra step. If that’s what’s called for within the context, isn’t that our job as comedians?’

Like most struggling people in the arts, he also had to take other supplementary jobs that he didn’t want, being employed as a Mall Santa Claus on one occasion. He told Contactmusic.com, ‘I have some experience playing Santa Claus. When we were in the Groundlings together, Chris Kattan was my elf at this outdoor mall in Pasadena for five weeks, passing out candy canes. It was hilarious because little kids couldn’t care less about the elf. They just come right to Santa Claus. So by the second weekend, Kattan had dropped the whole affectation he was doing and was like, in the voice of boredom, “Santa’s over there, kid.”’ Will also began working at an auction house thanks to an offer from Viveca Paulin – a friend, who would soon become his wife. It was a job that had its bonuses, particularly for a struggling actor. It meant that he could attend auditions while also taking home a steady pay cheque.

Small roles followed – none of them notable – but they did include roles in TV shows such as Grade Under Fire and Living Single. There was also the low budget movie A Bucket of Blood. The little-seen film was directed by Michael James and starred former Brat Pack star Anthony Michael Hall. The 1995 movie was a remake of the 1959 cult classic by legendary budget producer Roger Corman. The horror comedy focuses on the story of an unpopular busboy who turns to murder to make his macabre sculptures. Ferrell plays a stoner-type character alongside David Cross, another comedian who would land larger roles – most notably as Tobias Funke in the acclaimed show Arrested Development. There were also several commercials.

During his time with the Groundlings, Ferrell performed at several venues but had no problem pinpointing his weirdest gig. Former American Football star and Naked Gun actor O. J. Simpson was accused of murdering his ex-wife Nicole Simpson and her friend Ronald Goldman in the nineties. Because of Simpson’s celebrity status it was always going to be one of the most public trials in history, but given the advent of 24-hour news it suddenly became a worldwide sensation.

While Simpson was finally acquitted, it took over eight long months before the jury finally got to make their decision. Will told comedian Jeff Garlin for his radio podcast: ‘When I was at the Groundlings Theater right down here on Melrose, we were in the show at the time during the O.J. trial. As everyone remembers, the jury was sequestered, they couldn’t go anywhere. So we performed for the O.J. jury in a courtroom. We did sketch comedy to 12 people. Which is really hard to do. Sketches didn’t have anything to do with court cases, we just did our show. They politely laughed. It was awkward. We were in a brightly lit courtroom in the middle of the day. Sketch comedy for 12 people. But they gave us a standing ovation. That was our public service.’

While there were fun elements, people who made the cut were under no illusion that this would be hard, gruelling work – aided by a ruthless edge. Teacher Jim Rash told Yahoo! Movies: ‘There are basically six levels: Basic, Intermediate, Advanced and Improv. And then you move into our Writing Lab series, and if you make it through all those elements, you are asked to join Sunday Company, which is basically our farm team. And you can spend anywhere up to a year and a half in the Sunday Company. And any time during that time, you may or may not be voted into the Main Company.’

Former Groundling and SNL star Maya Rudolph told The Hollywood Reporter: ‘The goal is to work your way into the [Main] Company. When you’re standing around in the hallway and you see all the pictures on the wall of the current Main Company members, I would see all these faces that I never saw [at the theatre]. I used to play this game – the people we’d literally never performed with, we’d go, “Get the fuck out, Get the fuck out, Get the fuck out.” We’re like, “Make room for us, we want to be in the Main Company, you know, get the fuck out, make some room for us kids.” Then, my second or third year on SNL, I get a call: “Hey, Maya, um, we need some more space in the Main Company, so would you mind stepping down?” I was devastated because I’d worked so hard to get there, but I knew she was right. I’m not there, I get it. I’m literally the creator of Get the Fuck Out. So I got the fuck out.’ And former Groundling star Chris Parnell added: ‘What is so great about the Groundlings is the process of elimination that happens all the way up the chain. You have got to get that mark of approval at every level. You might be asked to repeat the class, you might be asked to leave. So by the time you make it into the Sunday show, you are guaranteed that people are going to be at a certain skill level, and then in the Main Company, even more so.’

The Groundlings was an excellent comedy apprenticeship for Will. Because of Will’s success and countless others, it has been seen as a breeding ground for future Saturday Night Live stars. In 2012, for example, five of the Academy Award contenders, including Bridesmaids star Melissa McCarthy, original Bridesmaids screenwriters Kristen Wiig and Annie Mumolo, and Jim Rash and Nat Faxon, for their adapted screenplay of The Descendants, all began at the Groundlings. Comedy star Jim Rash, who is still a Groundling teacher, told Entertainment Weekly: ‘There are the people who want the instant gratification … “When is Lorne [Michaels, SNL supremo] going to drop by my class and discover me?” But we try to impress upon people we’re not here to teach you how to be funny. I don’t care if any of this stuff is funny. I just want to see the story.’ The Groundlings was seen by many comedians as a natural stepping stone, like amateur football before trying to make the big leagues. Comedienne Kathy Griffin remembered to The Hollywood Reporter: ‘The night Lorne came, Lisa Kudrow, Julia Sweeney and I were all auditioning for a spot, and he picked Julia. Lisa and I were crying that night at a diner somewhere. [Later] I was on a little show called Suddenly Susan for four years; it changed my life. She became fucking Phoebe [in Friends]! We didn’t understand there were other things. We all thought it was only about getting on SNL.’

She added: ‘We had to audition our sketches for one another before they went onstage. And, let me tell you, that’s a Michael Vick dogfight right there. So you’re with your friends and you guys all love each other, but it’s extremely competitive. It’s like football. And there are cuts just like football at every single level, and it’s all about not getting cut. And then once you don’t get cut, trust me, you never get comfortable. Because the weekend Lorne Michaels comes, you want to be picked.’ Comedienne Tracy Newman added: ‘I think that once the Groundlings became the training ground or a farm company for Saturday Night Live, the group dynamic and camaraderie probably disappeared to a certain extent. It became a little bit dog-eat-dog. Even when I was there, it was already starting to be dog-eat-dog.’

While Ferrell would end up performing many years in the famed 30 Rock (30 Rockefeller Plaza, the address of the GE Building which houses the NBC Studios), performing with the Groundlings didn’t necessarily mean a future at SNL then. He was desperate to become the latest SNL member, but it would mean a long audition before he finally got his chance to follow in the footsteps of some of America’s most legendary performers.