7 Times Famous Bosses Were Insanely Generous

To commemorate Nick Cannon's Like A Boss premiering March 29 at 9/8c, we've rounded up seven spectacular stories. 

Sometimes, your boss will suprise you with a fancy lunch, a special opportunity or a great bonus. Chances are, you might have experienced the generosity of a benevolent boss. But you haven’t truly been touched by insane generosity the way the employees of some of these famous bosses have. To commemorate Nick Cannon’s Like A Boss premiering Tue., March 29 at 9/8c, we've rounded up seven times famous bosses were insanely generous. 

1. Taylor Swift

Making friends on Hamilton Island

A photo posted by Taylor Swift (@taylorswift) on

Taylor Swift knows how to run a squad, and she knows how to do right by her professional crew too. When her epic 1989 World Tour was winding up, Tay treated her entire crew with a holiday to Hamilton Island on Australia’s Great Barrier Reef to thank them for the tour’s success. She posted a pic from the vacation to Instagram, writing, "So stoked to be able to take my band and crew on a vacation at the end of a long and wonderful tour. For all their hard work this year, they really deserve it. Thank you to Hamilton Island for taking such great care of 125 of the people who work tirelessly to make sure the 1989 World Tour stage gets built, the lights are on, the costumes are made, the guitars are tuned, and the show goes on.” Footing the bill for 125 people on a luxury vacation, by the way, is not cheap.

2. Jessica Alba

Jessica Alba’s Honest Company has a $1 billion dollar valuation, so she'd be right to be generous to her employees. Alba offers new parents—both moms and dads—16 weeks of paid maternity leave, which might not seem that generous (if you live somewhere where maternity leave is required by law), but in the States, only 12 percent of private sector employees have access to paid parental leave. It’s an ongoing, holistic generosity that shows just how much Alba values not only her employees, but their families, and their commitments outside work.

3. Oprah

Oprah generosity stories are like fairytales—everyone knows them. Outdoing herself entirely, Oprah bought her entire staff of over 100 employees luxury 10-day cruises in the Mediterranean. It doesn’t end there—the tickets weren’t just for her staff, but for their friends and family members as well! Apparently, the price tag on Oprah’s generous gift to her employees was over $750k.

4. Adam Sandler

It must be nice to work for Adam Sandler. On Grown Ups, the movie which Sandler co-wrote and produced as well as acted in, the comedian really splashed out on his co-stars, who were also technically working for him. After filming wrapped, Sandler bought each of his 4 co-stars a £160K Maserati. Talk about bonus! 

5. Jennifer Hudson

Remember when J-Hud was in the Sex & The City movie as Carrie’s assistant, and Carrie bought her a bag? Well Jennifer Hudson, as a boss, is even more generous than her fictional boss, buying her assistant, Walter Williams, a whole house for Christmas. The two are actually childhood friends who met in the 6th grade, so Hudson’s gift went both to an employee AND a friend, which makes it all the more adorable.

6. Katy Perry


Katy Perry looks like a lot of fun to work for (a lot of her staff are old friends), and it turns out she’s a pretty generous boss too. She allegedly gave her whole staff of assistants an electric car each. The green friendly cars racked up a bill of $500,000 for Katy, as she bought five in total. The cars were luxury, 4-door Fisker Karmas, which are pretty damn splashy--and environmentally friendly, so Katy was being generous to her staff and to planet earth at the same time!

7. David Bowie


Even in death (r.i.p.) David Bowie was a generous boss. As well as leaving parts of his $100 million estate to his wife and children, Bowie left a generous bequeathment to his personal assistant and his son’s former nanny. His assistant and close friend Corinne "Coco" Schwaband was left $2 million, and his son’s former nanny, Marion Skene, was left $1 million. Even in his will, Bowie didn’t forget to show his appreciation for his employees.



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