Shirley MacLaine Hiring PA To 'Drink Cocktails': Star, 91, Wants 5pm 'Wingman'

Shirley MacLaine is proving once again that she's in a league of her own. The Oscar-winning star, now 91, is reportedly hiring a personal assistant — but not just any assistant.

According to insiders, the Steel Magnolias icon wants someone who can help with errands, keep her company and, most importantly, share cocktails with her every evening at precisely 5 pm.

The unusual request has sparked both amusement and admiration online, reinforcing MacLaine's reputation as one of Hollywood's most delightfully unconventional stars.

A Job Description Like No Other

Sources say MacLaine's new assistant won't just be organising schedules or managing daily tasks.

The role requires the ability to sit with her at the end of each day, sip drinks and talk about her legendary career.

One insider described the position as 'part confidant, part bartender and part wingman,' adding that whoever takes the job must be ready to discuss her films and listen to the kind of stories only a Hollywood veteran can tell.

According to the Daily Mail, MacLaine has made it clear that companionship, conversation and shared cocktails are non-negotiable.

The Actress Embracing Companionship In Her 90s

Friends say MacLaine has become increasingly reflective in recent years. RadarOnline reported that she's willing to pay well for someone who will join her nightly cocktail hour while she reminisces about decades spent on film sets and among stars.

The request highlights both her humour and her desire for genuine connection — a contrast to the more transactional assistant roles typical in Hollywood. It also touches on the reality many ageing celebrities face: a quieter life where meaningful human interaction matters more than ever.

A Career Worth Sipping To

MacLaine's seven-decade film career includes classics such as The Apartment, Terms of Endearment, Sweet Charity, and Steel Magnolias.

She has won an Academy Award and earned multiple nominations, while also becoming known for her sharp wit, spiritual outlook and unapologetically eccentric persona.

For any film buff, the chance to share 5 pm cocktails with her is a front-row ticket to Hollywood history. As NewsBreak reported, she has even shared a list of requirements with friends to ensure applicants understand the role's personal and intimate nature.

The 5pm Cocktail Tradition

The timing of her ritual is precise: drinks must be poured at 5pm every day. MacLaine has reportedly maintained this tradition for years, valuing the calm, conversation and comfort it brings.

The assistant's role would include mixing cocktails, keeping her company and indulging in stories about her life, movies, philosophies and the characters she's encountered along the way. It's a job that merges practicality with companionship — precisely the sort of arrangement MacLaine has always favoured.

Fans Applaud Her Honesty And Humour

News of the job posting has gone viral, with fans calling it 'the dream role' and praising MacLaine for her candour.

Thousands joked they would apply on the spot, while others noted the bittersweet undertone: the loneliness that can accompany ageing, even for someone as legendary as she is. Still, most agreed the role perfectly captures her bold spirit and refusal to conform to Hollywood expectations.

The Most Shirley Maclaine Job In Hollywood

MacLaine has never hidden who she is — quirky, outspoken, spiritual and defiantly independent.

Her search for a cocktail-sharing assistant isn't a gimmick; it's an extension of her personality. At 91, she remains unafraid to ask for what she wants: good conversation, good company and a well-made drink.

For whoever lands the role, it will be far more than a job. It will be a nightly audience with a Hollywood legend — served with a martini.