Hey, {{first_name | friend}}!
In honor of National Boss's Day (October 16), we're celebrating the people who make the workplace what it is, for better or worse. From inspiring real-life leaders to fictional managers who would give HR nightmares, we've rounded up six movies, books, and TV shows featuring unforgettable bosses. Whether you love your manager or can't wait to clock out, there's something here for you.
Want even more picks? Try Pix Plus free for 7 days for 4+ newsletters from our entertainment writers with strong opinions and even stronger recommendations. Plus no ads, ever.
Quick Links
Every pick is independently selected by our editors. If you buy something through our links, we may earn a commission.
Iconic TV Bosses We Love (and Loathe)
Some bosses make you excited to come to work. Others make you question every career decision you've ever made. These two TV bosses fall on either side of the spectrum.
Bob's Burgers
Streaming on Disney+
If there's one fictional boss who deserves a little appreciation this National Boss's Day, it's Bob Belcher (H. Jon Benjamin). Between keeping his struggling burger restaurant afloat and managing his wonderfully chaotic family, Bob's patience is constantly tested. But his dedication, kindness, and love for his family make him impossible not to root for.
Severance
Streaming on Apple TV
Your boss may be bad, but have they ever pretended to be your friendly next-door neighbor just to spy on you? Patricia Arquette plays the deeply unsettling Harmony Cobel in this acclaimed sci-fi thriller about employees whose memories are surgically divided between work and personal life. A perfect National Boss’s Day watch that'll make you appreciate your own manager a little more.
Hotel Spotlight
Together with Inside Hotels
The Maybourne Beverly Hills
The Vibe: Quintessential Cali luxury
The Location: Beverly Hills, CA
Instaworthy Accommodations:
In the heart of Beverly Hills’ Golden Triangle, The Maybourne Beverly Hills offers refined elegance with a distinctly European sensibility. Newly renovated rooms and suites, designed by Bryan O’Sullivan, feature light-filled interiors, bespoke furnishings, and a soft Californian palette, with many offering private balconies and city views. Guests can unwind at the rooftop pool and cabanas, dine al fresco at The Terrace, or retreat to the expansive spa, complete with a serene mineral pool. Just steps from Rodeo Drive, The Maybourne delivers a polished stay in one of Los Angeles’ most prestigious neighborhoods.
Bosses Worth Reading About
What does it take to be a truly great boss? These two inspiring true stories highlight business leaders who challenged conventional management practices by putting their employees first.
Let My People Go Surfing
by Yvon Chouinard
Try to imagine a boss who actually encourages you to ditch work and go surfing. Patagonia founder Yvon Chouinard built his company around that very philosophy. In this inspiring memoir, he shares how prioritizing flexible work schedules, employee well-being, and environmental responsibility helped create one of the world's most successful outdoor brands.
Everybody Matters
by Bob Chapman
When Bob Chapman took over manufacturing company Barry-Wehmiller, he set out to prove that businesses could thrive by treating employees as people to care for rather than expenses to manage. In this inspiring book, Chapman shares how he challenged traditional management practices, built a culture of compassion, and redefined what it means to be a great boss.
Hotel Spotlight
Together with Inside Hotels
Omni Hilton Head Oceanfront Resort
The Vibe: Coastal bliss
The Location: Hilton Head Island, SC
Instaworthy Accommodations:
At Omni Hilton Head Oceanfront Resort, you can choose between 323 beautifully appointed guest rooms and suites, each with tropical-inspired decor, modern amenities, and breathtaking views of the Atlantic. With access to 11 miles of lagoon trails, 24 pickleball courts, private beaches, sparkling swimming pools, and wellness areas, you’ll never want to leave this tranquil escape. However you spend your days, be sure to try the succulent surf and turf at HH Prime for dinner. Or, if you’re feeling adventurous, indulge in a culinary adventure with Chef’s Playground, a surprise four-course meal!
The Good, the Bad, and the Bossy
Some bosses inspire greatness. Others inspire resignation letters. These two workplace comedies feature larger-than-life leaders who steal the show.
The Devil Wears Prada
Streaming on Disney+
Aspiring journalist Andy Sachs (Anne Hathaway) lands a dream job assisting the notoriously demanding editor of a prestigious fashion magazine. Meryl Streep is unforgettable as Miranda Priestly, the ice-cold boss whose impossible expectations and devastating one-liners make this workplace comedy a modern classic.
Late Night
Streaming on Prime Video
A legendary late-night host's career is on the line when she hires an inexperienced new writer to help revive her struggling show. Emma Thompson and Mindy Kaling are a delightfully mismatched duo in this hilarious and surprisingly heartfelt comedy. Plus, it feels reminiscent of HBO’s Hacks, which is quite the compliment.