Outrageous Week continues as Liam Rātana journeys through the 20 moments that defined the series. 

Note: This article contains plot spoilers for a series that ended over a decade ago. You have been warned. 

I was 10 years old when Outrageous Fortune debuted on our screens, but my bed time was strictly when Shortland Street finished. I caught glimpses of the West family’s escapades here and there, but it wasn’t until over a decade later that I got to watch the series properly. At the time, my ex-girlfriend and I were staying in a state house in Mount Roskill, both young, broke, and bored, and we found solace in the relatable comedy-drama. The first couple of episodes were equal parts entertaining, funny, and ridiculous. We were hooked, finishing the entire series in just a couple of weeks. 

There were many reasons why I appreciated watching the show so much in my 20s: the offensive humour, the west Auckland setting (I lived in west Auckland for five years as a teenager) and the multiple subplots – Ted’s history as an expert safecracker, Loretta’s cunning entrepreneurial skills, and Munter and Van’s bromance. The show so aptly captures the culture of New Zealand and the era it was made, from the cars, to the music, to the boganism and the multiculturalism. As the iconic show celebrates turning 20 years old this week, here are 20 outrageous moments that defined the series.

1. Wolf’s four-year sentence (S01, E01)

Wolf’s arrest is the inciting incident for the entire series, forcing Cheryl to take control and the rest of the family to reevaluate their lives. As the archetypal criminal patriarch, Wolf’s removal from the West household sets off a domino effect. It is both a plot device and a thematic statement: what happens when the kingpin is dethroned?

2. ‘It all stops. From now on, we play it straight.’ (S01, E01)

The entire premise of Outrageous Fortune hinges on this one bold decision. When Wolf is sent to prison, Cheryl declares that the family will abandon their criminal ways and live life on the straight and narrow. It’s a turning point that sets the tone for the entire series: a chaotic, blackly comic journey of a crime family trying (and frequently failing) to reform. The irony is that going straight often proves more difficult than a life of crime, creating endless narrative tension and character growth.

3. Judd gives Cheryl the Hoochie Mama money (S01, E10)

Detective Wayne Judd plays an unusual role in the Wests’ lives – a symbol of the law, but also someone drawn into their chaos. When he calls Cheryl honest, it’s a surprising moment of tenderness and validation. His funding of Hoochie Mama with dirty money from a bust isn’t just a romantic gesture; it’s a vote of confidence in Cheryl’s legitimacy and integrity.

4. Judd and Cheryl hook up (S01, E11)

When Cheryl finally sleeps with Judd after his persistent advances, it’s a massive shift in the narrative. It marks her departure from the loyal wife and blurs the line between law and lawlessness. Judd becomes emotionally and professionally compromised, declaring his love for Cheryl, who finds herself in an even murkier moral territory. This moment reshapes both characters, deepening the emotional stakes of the show.

5. Van and Aurora’s relationship (S02, E06-S03, E04)

Van West is often portrayed as the dumb twin and village idiot but his relationship with Aurora shows Van’s emotional depth. Their romance is passionate, tumultuous, and ultimately doomed. Aurora challenges Van to grow but also reminds us that tragedy is never far from the Wests. Her sudden death – struck by a bus while trying to hide Tyson’s drugs – is among the most devastating moments in the series. It’s the kind of jarring tragedy that Outrageous Fortune does so well, reminding viewers that actions have consequences. For Van, it’s a descent into grief that reshapes his outlook forever.

6. Loretta’s erotic film debut and hookup with Hayden (S02, E11)

After running a series of semi-successful illegal business ventures, Loretta seemingly finds her true calling. Hayden demands Loretta film a porn video he has scripted, which Loretta trashes and rewrites. She ends up enjoying the director role and her and Hayden end up sleeping together. It’s one of the show’s most shocking yet surprisingly authentic relationships – a pairing is as twisted as it is fascinating. It shows us that Loretta does indeed have feelings and sets off a series of morally ambiguous decisions – parenthood, arson, revenge. Their dynamic mirrors the show’s recurring tension between intellect and impulse, control and chaos. It showcases her defiance, intelligence, and refusal to conform to societal expectations. This subplot underlines the show’s unapologetic embrace of sexuality and questions of autonomy.

7. The Wests visit Tutaekuri Bay (S02, E17/Christmas Special)

It’s Christmas, and the Wests are gearing up for their annual chaos at Tutaekuri Bay – despite Cheryl’s emotional spiral over Judd’s imprisonment, a surprise visit from her estranged sister Jeanette, and Pascalle’s dilemma over staying with Bruce. While Jethro opts out, the rest of the clan – including a rejuvenated Ted, lovestruck Van, and Loretta (abandoned by Hayden) – pile into Eric’s bus and crash the DOC campsite under a fake name, ignoring yet another ban. However, their usual spot has been claimed by the rival Doslic family, sparking a classic West-style turf war. 

8. Pascalle’s porn disaster (S03, E05)

Pascalle’s quest for glamour and validation often led her down misguided paths, but none more painfully than her involvement in Loretta’s adult film. Hoping to raise money for hymen reconstruction surgery before marrying Bruce, Pascalle agreed to appear on camera – only for Bruce to discover the footage and end their engagement. For all her bravado and beauty queen dreams, this moment lays bare Pascalle’s vulnerability, exposing the emotional cost of chasing perfection. It’s a turning point that peels back the glossy exterior and reveals a far more complex, broken-hearted young woman beneath.

9. The launch of The Tool Guys (S03, E16)

When Van and Munter decide to “go straight” by launching The Tool Guys – a 24/7 handyman service – it’s a hilarious and oddly heartfelt milestone. Their earnest attempt at legitimacy, complete with homemade flyers, T-shirts, and vague branding, leads to them being mistaken for male sex workers. While this could’ve been a one-off gag, the storyline grows into a genuine business venture, complete with clients, staff (including The Gooch and Aaron Spiller), management drama (cue Loretta), and even romantic chaos. The Tool Guys becomes a recurring symbol of the Wests’ tug-of-war between crime and respectability. It also deepens the bond between Van and Munter, offering some of the series’ most endearing and comedic moments – including a disastrous bathroom hookup that somehow ends in a marriage proposal. Ultimately, The Tool Guys captures the show’s core: well-meaning Westies trying to better themselves while being gloriously incapable of leaving the chaos behind.

10. Milt’s sudden death (S04, E2)

Pascalle’s whirlwind romance with the ultra-rich Milt ends abruptly when he dies of a heart attack. The death transforms Pascalle into a wealthy widow and disrupts the family dynamic. Suddenly, she holds the financial power – but it comes at a personal cost. The show balances absurdity with grief in a way that only Outrageous Fortune can.

11. Cheryl says goodbye (S05, E17)

In one of the series’ most heartbreaking episodes, Cheryl loses her baby with Judd and retreats to Tutaekuri Bay – the place where she and Wolf scattered the ashes of their first child. Consumed by guilt and grief, Cheryl struggles to carry the weight of another devastating loss. But, driven by her deep sense of duty to her family, she summons the strength to return home and say a final goodbye, marking a moment of raw vulnerability and quiet resilience.

12. Drug container drama and Jethro on the run (S04, E03)

Jethro steals a container full of illegal steroids from Wolf on behalf of his mother. Van and Munter accidentally destroy the steroids and Wolf finds out, forcing Jethro into hiding. The botched job is symbolic of his arrogance and marks a turning point in his downward spiral. It’s one of the show’s tensest arcs, combining crime drama with family fallout.

13. Jethro’s return (S04, E18)

Whenever Jethro resurfaces after one of his morally bankrupt absences, it creates an immediate shakeup. His slick, ambitious persona is the perfect foil to Van’s sincerity. His returns usually mean trouble, but they also provide some of the show’s sharpest insights into family loyalty, greed, and redemption. One of Jethro’s most outrageous moments is when he returns dressed as Van to orchestrate a bank robbery, successfully framing Wolf. He also gets Sheree pregnant while impersonating Van and later returns with Wolf to disrupt Ted and Ngaire’s wedding, leading to a complex series of events involving Nicky and Pascalle.

14. Sheree and Nicky conspire (S05, E11)

This unlikely and toxic alliance nearly destroys the Wests from the inside. Sheree, manipulative and cunning, aligns with the even more dangerous Nicky Greegan. Their schemes push the West family into chaos, sparking betrayal, paranoia, and violence. It’s one of the show’s darkest and most suspenseful chapters. 

15. Loretta chooses Jane (S05, E19)

After the stillborn death of Cheryl and Judd’s son, Hayden and Loretta get back together. They want more control over their daughter Jane from Cheryl, who agrees to allow them full custody of Jane if they get married. Loretta’s arc from cynical teen to reluctant mother culminates in her choosing to keep her daughter Jane. It’s a moment of surprising softness that reveals the depth beneath her icy exterior. Cheryl’s support during this time also rebuilds their fractured relationship, underscoring the central theme of maternal love.

16. Cheryl stabs Zane Gerard and Pascalle is shot (S5, E19)

A raid led by detective Gerard erupts into violence and ends with Cheryl stabbing him in self-defence. It’s a moment of high-stakes drama that pushes Cheryl into a legal and emotional crisis. Gerard’s corruption is finally exposed, but Cheryl’s hands aren’t clean either. Pascalle is caught in the crossfire and shot. The chaos of the Wests’ lives reaches a literal breaking point, and the near-death of one of their own brings a rare moment of vulnerability. It’s a reminder of how their actions endanger everyone around them. Gerard succumbs to the injuries from Cheryl’s stabbing, setting off a murder investigation that implicates the entire family. The fallout is massive – testing loyalties, reshaping relationships, and forcing the Wests into hiding or exile. It’s one of the show’s most suspenseful and morally complex plotlines.

17. Cheryl pleads guilty to murder – and the family spirals (S06, E1)

The final season opens with a shockwave: Pascalle is recovering in hospital, Cheryl is facing a murder charge after stabbing Detective Gerard, and Van steals and vandalises a police car in a fit of rage. But the real gut punch comes in court when Cheryl, wracked with guilt, unexpectedly pleads guilty to murder. Her stunned family can’t make sense of it, and Loretta is left to clean up Van’s mess by torching the evidence. It’s a chaotic, emotionally loaded opening that rips the safety net from under the Wests and sets the stakes for the show’s final run – what happens when Cheryl is no longer there to hold them together?

18. Judd and Pascalle have an affair (S06, E10)

One of the show’s most outrageous moments comes not from a criminal act, but from yet another unlikely romance: when Judd, Cheryl’s partner and the family’s unlikely moral compass, begins an affair with Pascalle. It’s a bombshell twist that fractures the Wests from within, derails Cheryl and Judd’s already strained relationship, and upends Pascalle’s arc entirely. For a show built on blurred moral lines, this moment pushes things into treacherous new territory. It’s not just betrayal – it’s taboo. And yet, true to form, Outrageous Fortune doesn’t play it for shock value alone. The fallout is raw and devastating, particularly for Cheryl, who is left reeling in prison. It’s a moment that redefines loyalties, relationships, and what the show is willing to risk in the name of character drama. Simply put, this is the point where no one is safe anymore – from each other.

19. Jethro redeems himself (S06, E17)

After years of scheming and selfishness, Jethro finally steps up for his family in the penultimate episode of the series. In a rare moment of moral clarity, Jethro plays peacemaker, persuading Cheryl to reconcile with Pascalle and redirect blame toward Judd to protect the family’s legal case. When Judd later brings him the damning police report on Detective Gerard, Jethro discovers that Bailey had withheld it for her own gain. Disgusted, he forms a temporary alliance with his longtime rival Judd to ensure the report is used strategically. Leveraging this new power, Jethro forces Bailey to follow his lead in court, ultimately helping to clear Cheryl of her charges and restoring her at the heart of the West family.

20. The final farewell (S06, E18)

The series ends with emotional goodbyes and new beginnings. Cheryl remains the heart of the family, Van finds love and stability, Pascalle leaves with Judd with one last piss off the deck from Ted. Loretta, Hayden and Jane settle into their own messy version of family. It’s an ending that’s imperfect – like the Wests themselves – but deeply satisfying.

Click here to read the rest of our Outrageous Week coverage as we celebrate the 20th anniversary of the series. Watch Outrageous Fortune here on TVNZ+ or on the Outrageous Fortune YouTube channel.