Lies That Chelsea Handler Told Me (16 page)

When Friday came, I told Beth I needed to talk to her, but she said she really needed to tell me something first. Knowing that I was delivering nothing she wanted to hear, I decided I should probably build up as much goodwill as I could, so I let her do the honors.

“I lost ten thousand dollars,” she said.

Uh… what? I’m sorry, it sounded like you said you lost ten thousand dollars, but I know there’s no way that’s possible, because we don’t have ten thousand dollars for you to lose. I know some of you are thinking, “What do you mean you don’t have ten thousand dollars to lose? That’s nothing. You’re on TV and rich.” One of those is true. Let’s just say that with a lot of my checks, after I pay The Man, my agent, lawyer, and manager, I barely have enough left over to get drunk. But make no mistake: ten thousand dollars is a lot of fucking money.

“I don’t understand,” I said. “How did you lose ten thousand dollars?”

“Well, Chelsea and I bet on a basketball game last week and won.” What? They bet a basketball game last week? How did I not know about that? “We bet one more Monday and won.” What in the fuck is going on here? “So, I thought I would try one on my own, and I lost. I’m so sorry, baby. I don’t know what I was thinking. I was winning. It all seemed so easy, like I could never lose.”

Oh. My. God. This was not the conversation I thought I was going to have. Ten thousand dollars?

I called Chelsea. “Beth lost ten thousand dollars.”

Silence.

“Did you hear what I said?”

“I heard you,” she responded. “That’s not good.”

“No shit that’s not good. Why were you guys gambling?”

“Well, every fake bet I made I would have won, so I thought I’d try a couple of real ones,” she explained. “Beth kept calling and calling about when we were betting, so I let her bet with me. Ten thousand dollars. Wow. That’s a lot of money. I’ll call you back.”

Fifteen minutes later I got this text: It’s not $10K. It’s $15K. His name is Trent. 310-xxx-xxxx. I’m really sorry about this.”

Great. Fifteen thousand I didn’t have that I needed to shell over to a bookie. So I called him. I figured I could explain the situation and tell him that I’d pay it off in two installments. Now, I’ve been around enough bookies to know that normally there’s no way they would let that happen, but I figured I would drop Chelsea’s name and the guy would cut me some slack. I’ll cut right to the only quote you need to know from that conversation.

“I don’t care if you’re friends with the Pope. It’s fifteen K all at the same time.”

There was no getting out of this. Fifteen thousand dollars basically would wipe out my little cushion. But as much as we couldn’t afford to pay this guy, we had to pay this guy. Trent didn’t strike me as a dude who was going to let $15K just walk away. The next day, I set up a time to go over to his house and then went to the bank to get the money.

You ever write a check big enough for you not to want to let go of it? Imagine that… but with cash. I had fifteen thousand dollars in cash in my hand. I’d be lying if I told you the idea of driving to Mexico and seeing how long I could be drunk off $15K didn’t at least flash through my mind. And by flash, I mean I thought about it for about twenty-five minutes.

I drove up to Trent’s house in the Hollywood Hills; he buzzed me in at the gate and told me that he was in the back by the pool. As I was walking around the house all I could think was how I’d dug my own grave on this one. I never spoke up and because of that I was out $15K. I also decided that, to save my own ass, I would never tell Beth about the joke. Ever. That was the one good thing. She felt she had to make it up to me because she was the one who’d fucked up.

Nothing in the world could’ve prepared me for what I saw when I turned the corner and entered Trent’s backyard. It was Chelsea and Beth. Sitting on chairs by the pool.

“What’s up, asshole?” Chelsea said.

I was too stunned to speak.

They had set me up from the beginning. As soon as I had told Beth that Chelsea was a big-time gambler, Chelsea pulled the ol’ switcheroo. That tricky bitch.

Who knows? Maybe I am adopted.

Josh should be ashamed of himself. His wife is the sweetest person I have ever met, and it’s unfortunate he found himself in such a jam. I believe I am singlehandedly responsible for saving their marriage. Godspeed.

—Chelsea

SHOSHONNA HANDLER

My name is Shoshonna and I am Chelsea’s older sister. My parents told me that before Chelsea was born I was a cute, good-natured, happy-go-lucky kid. Then came 1975 and my blissful little five-year-old world was turned upside down. I had been the baby of our large and dysfunctional family for five years and had loved every minute of it. I didn’t know what to make of the new addition to our family, or why they would have named her Chelsea. Every time I heard her name, it reminded me of seafood stew. I cried all the time.

Chelsea had an all-consuming presence. It felt like being hit by a train. My father has told us all many times over that when she was born, she came out with such a strong cry that the nurse said to him, “You’d better watch out for this one.” Over the years, I became more quiet and pensive as Chelsea’s boisterous personality took center stage. She was full of piss and vinegar from day one, and could throw a tantrum that would put any toddler to shame. This kid was a force to be reckoned with, and my parents were already exhausted with their other five kids. They were in no way prepared to handle raising this particular child, and their feeble efforts were of little consequence. Besides, our mom was always napping, knitting, or cooking, and was too soft-spoken to really stand up to Chelsea.

By the time Chelsea was three, she had the street smarts of a nine-year-old, and I may as well have been born yesterday. We were complete opposites, like oil and water, and never agreed on anything. If I was watching a TV show she didn’t like, she would say something like “A package just came for you at the door, Shana,” or “Mom just took some brownies out of the oven,” and then take over the television. I fell for it every time. I would come back in the room and wage war in the form of a wrestling match. Ultimately I would be the one to get yelled at or sent to my room because I was “older” and “should know better.” We fought constantly and wanted to rip each other’s throats out for most of our childhood. Physically I had the upper hand, but verbally I was no match for her. By the time she was eight, she had the debating skills of a seasoned politician, and I am being completely serious.

For many years we shared a bedroom, and we agreed to place masking tape down the middle and not cross territories. This was pretty much a joke, unless we were both in the room. Raids occurred when the other person was not there. Chelsea would regularly steal my clothes when I was in high school. (Yes, it’s true, she’s five years younger, and we were clearly different sizes, but this did not deter her. She would just knot the shirts at the waist or cut them in half.) At one point I installed latches to hold a combination lock on my closet door. A week later I came home from school to find her wearing the brand-new clothes I had just purchased with my first paycheck from my new afterschool job at the mall. I went nuts and ran upstairs to find that she had taken a screwdriver to the latches. And because she was so angry I wouldn’t share with her, she decided to tie-dye all my underwear.

Years later, when Chelsea was about fifteen and I was twenty and home from college, it was with great joy that I picked up the phone and heard a police officer tell me that they had Chelsea down at the station for shoplifting underwear at Sears with a friend. Underwear has always been a big theme in our family. Not wearing any can and has resulted in humiliation, in the form of photographs, e-mails, and/or having you and your genitalia chased around the house with salad tongs.

My parents weren’t home the day I got the call, and if I went and picked Chelsea up and kept it under wraps, she would owe me big time. I drove very slowly down to the police station with a big old grin on my face. I had had a good time at college, but this would definitely be the highlight of my life since graduating from high school. I was still smiling when I got to the police station and Chelsea got in the car.

It didn’t take her long to pronounce, “I know what you’re thinking, and I’d rather tell Mom and Dad the truth than be beholden to you for anything. So if you think you’re going to pull something over on me, you’re mistaken. I would rather lose my virginity to Craig Slass than owe you a favor.” Craig Slass was our next-door neighbor, who would easily have had sex with any one of us, if we had permitted it. He spat when he talked, was always drooling, and had what Chelsea referred to as a “woman’s ass.”

Our parents had a modest second home on Martha’s Vineyard, and every summer, as soon as school let out, our mom would head up there with all of us six kids and whatever dog we had at the time, in our awful van with blue vinyl bench seats. We would spend the entire summer there each year. Our father would come up every ten days or so and stay four or five days and then return to his bustling used-car business in New Jersey.

One summer on the Vineyard, I told Chelsea we were setting up a lemonade stand at the end of our dirt road so we could make a little extra spending money. I was twelve and she was seven. Things at the stand were hopping for an hour or so, and then sales fell flat. Chelsea, clearly bored, thought we should spice things up with a big sign for a raffle to meet Carly Simon, who lived on the Vineyard, too, but whom we did not know.

“It will get things moving around here,” she said.

“But that would be a lie, Chels…”

“So what? No one is going to actually win the raffle, retard.”

“But what if the police come around? I don’t know about this.” I was always a big worrier.

She looked at me with disgust. “The Martha’s Vineyard Police are not concerned with the two of us, Shoshonna. They have bigger problems than a twelve- and a seven-year-old selling lemonade and fake raffle tickets. Why are you such a Debbie Downer?” This was what Chelsea called me, and still calls me to this day when I bring up a point she doesn’t think is necessary to discuss.

Things did pick up a little with the raffle sign prominently displayed. We found ourselves fielding a lot of questions about Carly Simon, but Chelsea was always fast on her feet and had an answer for everything. I let her handle it. Of course, some of her answers were ridiculous, but who was going to challenge a seven-year-old?

At one point, a lady on a bike stopped and bought a lemonade and a raffle ticket and asked us if we thought Carly might sing for her if she won the raffle. Chelsea replied, “Not too many people know this, but Carly has very bad stage fright. You have to catch her on the right day. Some days she’ll sing and some days she won’t. It depends which way the wind blows.”

Another woman asked when she would be able to meet Carly Simon, since she was on Martha’s Vineyard for only a few weeks. “It’s not a problem,” Chelsea assured her. “Carly and I are very tight. She’s on tour right now, but I am in constant contact with her manager, and I am sure we can set something up.” The look on this woman’s face was priceless.

After another hour went by, things were dead again. It was then that Chelsea “accidentally” knocked over the change jar, pocketed most of the money when I wasn’t looking, and said she had to go to the bathroom and would be right back. She did not return. I ended up having to cart the table, chairs, signs, and pitchers on our red wagon solo down the very long dirt road back to the house. I later found out that Chelsea had hightailed it with our money into town on her banana-seat bike and treated herself to a buttered bagel and a Coke and then blew the rest of the dough at the arcade. You might think that no parent would have allowed their seven-year-old to ride into town alone on a bike and hang out. Well, with my parents it was pretty much a free-for-all, and it was 1982 and things were pretty loosey-goosey on the Vineyard. We hitchhiked all the time and it was no big deal. We never would have dreamed of doing this back in New Jersey, but for some reason, on the Vineyard, it was okay.

When she got back, I yelled at Chelsea and told my parents what she had done. Chelsea said lemonade stands were for chumps and the real money was in babysitting.

“Hello, who is going to let us babysit? We are way too young,” I replied.

“Listen, Shana, if you lost your goody-two-shoes looks, we could easily get you up to age fourteen. I could pass for ten. I’ll say I’m your assistant, and we’ll split the profits sixty/forty. Sixty for me, since it’s my idea.” Chelsea had already inherited some of my used-car-dealer father’s warped reasoning, and it was maddening to deal with.

“Maybe in a few years, girls, not just yet,” my mother wisely chimed in. “Stick with the lemonade stand for now.”

We had three older teenage brothers, and when we were up on the Vineyard, they got to sleep in the basement. The basement was the cool place to be. It had a separate entrance, its own bathroom, and a little fridge. It was like a clubhouse. My brothers’ names were painted on the walls, and there was thick shaggy carpeting and bunk beds everywhere. My brothers had a stereo and a million records and were usually playing Cat Stevens, Neil Young, or the Grateful Dead. There were even a couple of bongs down there, but we didn’t know what they were at the time. At least, I didn’t. Mom told us they were microscopes. She was completely clueless about drugs.

Our brothers had jobs during the summer, so they were often gone during the day. Chelsea and I would go down there and snoop around when we got bored. One day I found a rubber snake in my brothers’ stuff. Chelsea was and always has been petrified of snakes. She could not even see one on TV without crying hysterically. At the time, I’d had a rough few days of Chelsea’s shenanigans, and I wanted revenge. For weeks she had been daring me to drive an old two-door Datsun around our dirt road while my mother took her daily nap. It was a beater car that my dad left on the island year round. Chelsea had kept egging me on, calling me Goody Two-shoes and saying I was a giant sissy and that she would get her driver’s license before I did. I was sick of her teasing and finally drove the car just to shut her up, but of course, I dented the door on a big tree branch in the process. My father came up to the island the next day and went off on me, as Chelsea smiled devilishly behind him.