There’s no better feeling than seeing that last present wrapped, trimmed, and under the tree. Once the shopping is done, there’s nothing left to do but wait for the excited look on your loved ones’ faces when they receive their silk pajamas, MP3 player, video game, or gold necklace. But even if you’re sure your family and friends will love their gifts, there’s one sure way to shake your confidence—read the Neiman Marcus holiday wish book or any other aspirational luxury catalog. How could I ever have thought my dad would be happy with a new putter instead of a personal submarine? My mom’s cashmere robe will never compare with a Victoria’s Secret diamond-encrusted bra, and I know there’s someone on my list that would have loved that $25,000 cupcake car.
Sigh. There are plenty of stories of excess around the holidays to make us depressed about our little mall-bought baubles. But there are a few stories of largesse that we can all aspire to.
1. Sappy Simon
Thanks to his prickly persona on American Idol and the UK’s X Factor, Simon Cowell is richer than Midas. But underneath that brusque exterior is actually a kind and generous gentleman. In 2008, Cowell saw a three-year-old cancer patient and her family in a video on The Oprah Winfrey Show and decided to help. The family had been traveling 100 miles per day for their daughter’s radiation treatments and was financially at a dead end. As part of Oprah’s Big Give, Cowell stepped in and gave the girl’s family $162,000—enough to completely pay off their mortgage and allow them to focus their efforts on fighting the disease. He credited Oprah with teaching him to enjoy giving and said, “I never knew that doing good could feel so good.”
2. Here’s a Tip
In 1984, Robert Cunningham was a police detective and a regular at Sal’s Pizzeria, where waitress Phyllis Penzo had worked for over twenty years. One night, instead of a tip, Cunningham shared his lottery ticket with Penzo, agreeing that they would split the money if they won. Sure enough, each walked away with three million dollars when their numbers came up in the New York State lottery. Penzo got the call on April Fools’ Day and didn’t even believe it at first, but luckily Cunningham was a man of his word. At the time, he told People magazine, “I’ve been a simple person all my life. If I say I’ll do something, I do it. I hope money never changes me.” Their story became the basis for the movie It Could Happen To You, as well as a lifelong friendship.
3. A Bollywood Abode
Shahrukh Khan is one of the most successful actors in India, appearing in some of the biggest Bollywood hits in history. For over a decade, his trusted bodyguard Yaseen Khan has traveled and lived with him. But once Yaseen announced that he was getting married, Shahrukh realized that a man with a family would want his own house, so he bought the newlyweds a house as a wedding present. He bought an apartment close to his own, so that the two men could continue their working relationship. Now that’s a generous boss.
