Two and a Half Men had no dearth of interesting characters and a few of them were actually quite wealthy. Money was a prominent theme in the show, and the comedy took a painfully realistic look at how money divides a family and can also be a huge deciding element in relationships.
Charlie Harper, the main man for the first eight seasons seems to be a wealthy songwriter who owns a beach house in LA and is neighbors with Steven Tyler. But, after his death, it is revealed he has three mortgages on his house—but what about the other characters? Here are ten of the characters on the show ranked based on wealth.
Berta
Berta was the housekeeper of the Harper household and has been working for Charlie for many years. She continued working for the beach house when Walden bought Charlie’s home, and, though Walden paid her better, Berta wasn’t able to amass a lot of money.
She was responsible for quite a few people in her family, including her down-on-her-luck sister and one of her daughters and granddaughter. She was also shown to be generous, broadly speaking, and she often helped out her extended relatives. She wasn’t shown to be working anywhere else besides Walden's, and it’s unlikely that she had a second job, so, in spite of being financially independent, she likely was not too well off.
Jake
Jake wasn’t exactly financially prudent, although he does get a lot wiser as he grows up. He starts working for Walden’s company right after his graduation, but he doesn’t last long and doesn’t make any money from the job. He and his friend Elridge soon join the army and, over the next few episodes, very little information is shared about Jake’s profession or his post in the army.
He obviously starts out in an entry-level position, but, when the show ended, he had landed a posting in Japan and will obviously earn more when he is deployed.
Alan
Alan was a sneaky saver and even hid his secret cash stash from Charlie. However, it has been implied that he never saved enough to actually be financially independent. After season eight, his business goes seriously downhill; the two alimonies he had to pay to Judith and Kandi over the years had made a serious dent in his savings, so, after season nine, he is shown to be quite desperate.
Though Judith gets re-married and Alan doesn’t need to pay her alimony anymore, he still has to pay alimony to Kandi and support Jake. When the show ends, he is shown to be almost entirely dependent on Walden, and he is actually not shown practicing anymore, so it can be assumed he doesn’t have his own practice. He discovers Charlie's secret savings stash, but it may not be enough.
Judith
Judith stopped receiving alimony from Alan after she got married to Herb, and the show does not exactly divulge any details about her own personal funds. But, she did get quite a lot of assets in the divorce from Alan and had some family money, too, since her lifestyle was quite afordable, and she could obviously get by without the financial aid from Alan.
Plus, after she married the successful doctor Herb, they obviously joined their finances together, which only improved Judith’s savings.
Herb
There is no doubt that Herb was successful as a pediatrician, and he and Judith led a very comfortable life. Herb was financially pretty well-off and seemed to be a prudent saver. He had an independent practice in LA and could even afford a receptionist, which meant he earned pretty well.
Plus, he hadn't been previously married, so he didn't have to give alimony or child support to anyone. Despite their rocky marriage, Judith and Herb were never shown to be fighting about money, so their means possibly didn’t exceed the family’s income.
Lyndsey
The show never revealed details about what Lyndsey did for a living, although she did work for a bookie at some point. She received alimony and child support from her ex Chris, who was pretty rich. Lyndsey was seen leading a comfortable life and even took in Alan and Jake despite being aware of Alan’s financial woes, which means she herself was pretty well-off financially.
She throws some great parties in her LA home, and, even after her house burns down completely, she was able to arrange a decent home pretty soon after, which suggests she was quite comfortable money-wise.
Charlie
Charlie did have a pretty lavish lifestyle, and fans had often wondered how a moderately successful jingle writer could afford this massive beach house and so much luxury. He did find a sudden bout of incredible success with his Charlie Waffle stint which saw him earn good money as a children’s songwriter. But, after his death, it was revealed that his beach house had three mortgages, and, though he wasn’t in debt, he could not leave behind any sizable inheritance to any of his family members, so he could have been bankrupt in just a few years if he kept up these spending habits unless he got steady gigs.
Evelyn
Evelyn had worked as a real estate broker for more than three decades, and she mostly sold only to uber-wealthy international tycoons, which meant that she earned high commissions. She had an office and a pretty sizeable home, and she could afford high-end designer clothes and jewelry, which meant that she was likely quite wealthy.
She never quibbled with her sons over money, and, even when she was marrying Teddy, whom she thought was a multi-millionaire, she was fine with the prospects of keeping their finances separate. She often goes on expensive cruises and can afford cosmetic surgery and botox and also lent Alan some money for his Ponzi scheme without a second thought, which implies she was quite rich.
Rose
Many fans overlook the fact that Rose comes from old money and was richer than Charlie, whom she stalked for years. It was revealed in season three that Rose’s father was a very wealthy man who owned a bank, or possibly more. He lived with his mother in the family estate which was also in LA, which suggests that Rose was a trust fund kid.
Rose also reveals to Charlie that her family has business in London, and, although her trip to London was fake, this information could be real. Lastly, Rose, who is a psychology major, was able to get by for years without ever having a job, which obviously meant that she didn’t need to work.
Walden
Walden was a billionaire when he was introduced and he only got richer, making him the wealthiest character on the show. He had made his first million before he even turned 20 with an Internet venture, following which he made a website with Billy that Microsoft bought for $1.3 billion.
He also buys Charlie's beach house which must have cost him a fortune, and he also seems to have a lot of money to spare, as he is open to investing in things that he thinks could take off.