My Big Break- Part 3
The day I got the call to appear on Jimmy Kimmel, Jonas and I had been in the studio shooting some promos for the website, which had just been nominated for a Webby. The promos ranged from professional to sexy, since that was what our viewers had come to expect. In one promo, I played Tiffany as a sexy teacher while Jonas played Joanna as a sexy schoolgirl. In another, I played a sexy cop and held a surprised Joanna in handcuffs. By this point, I had been playing the Tiffany character for three years and it had become second nature to me. Since we were traveling more, I also now did my own transformations. Mara still helped out, but she couldn't travel with us whenever I had a piece to shoot so I was forced to learn how to become a woman on my own.
As we stopped to take a break from shooting, Doug called me over and told me I had an important phone call. When I picked up the phone, I was surprised to hear it was someone from "Jimmy Kimmel Live!" requesting I come on the show to shoot a few correspondents pieces. Without any hesitation I accept and thank the man for the opportunity. I told the rest of the guys about the phone call and they were all very excited for me. I also found out that Joanna had been invited to come on the show the following week. We finished shooting the rest of the promos and after changing back into Tim, they took us out to celebrate.
On the day of my first correspondents piece, I arrived early at the studio where I was met by Jimmy Kimmel and Guillermo. At the time I was dressed as Tim, so they instructed me to go backstage and change. When I reemerged as Tiffany, they set me up with a microphone and camera crew and soon I found myself on the street interviewing passersby about various entertainment topics. Between shooting, I was met by groups of fans who wanted my autograph and to pose for pictures. When the segment was over, I went backstage to change back into Tim and went back out to meet Kimmel. He told me that there was the possibility I could be back to do a regular segment if these first few segments do well on the show. I thanked him and went home where Gwen and my friends had arranged a viewing party for that night's episode.
"Tonight we have a new segment on the show," Jimmy Kimmel said when my segment came up, "By now a lot of you have probably seen the website TiffanyandJoannaDoAmerica.com. Don't worry, for those of you who haven't, it isn't as dirty as it sounds. On the website, which I hear is nominated for a Webby, two straight guys do interviews and profiles of businesses, concerts, and red carpet events dressed as hot girls. We actually tried that format on this show, right Guillermo?"
"Yes, Jimmy," Guillermo replied.
"Unfortunately for us," Jimmy continued, "People didn't want to see us as Jamie and Erma. It's too bad, I though I looked pretty sexy. Now next week, we have Joanna on the show, but let's go outside now to where Tiffany is standing by. Are you there Tiffany?"
"Hello, Jimmy," I watched myself say as Tiffany.
"Wow, it's hard to imagine that you are really a guy," Jimmy said, "Is it wrong that I'm a little turned on seeing you right now.? How did this all get started?"
"Well," I explained, "Our website was going nowhere until we did a profile on a salon that transforms guys into girls. People seemed to like Tiffany and I guess I've sort of been stuck as Tiffany since then."
"Well, you do a good job," Jimmy replied, "Now I understand you and your girlfriend got engaged. How is she with the other woman in your life?"
"She doesn't mind," I replied, "Just as long as she doesn't catch Tiffany in our bed."
"Oh, I'm sorry to hear that," Jimmy continued jokingly, "I bet viewers would enjoy seeing that."
"Well, I've tried," I joked, "She made it very clear she wasn't interested."
The interview went on a little longer and when it was over, I watched as Tiffany proceeded to interview various people on the street. Since it was a comedy show, I tried my best to gear the questions to get the funniest answers possible. At the end of the segment, everyone clapped and I was surprised to get a call from my mom. Now while my mom knew about the website, I wasn't sure how she felt about my dressing as a woman.
"Oh, Timmy," my mom said, "You looked so pretty on the TV tonight and you were so funny too. I admit I had my doubts about this before, but I'm so proud of you."
"Thanks mom," I replied.
We talked for a while and had a nice conversation. I also invited her to come with us to the Webby Awards ceremony and she happily agreed. My mother had raised me on her own and I had never met my father. Having no siblings, we were always there for each other and I loved her more than anything in the world. When I started playing Tiffany, I was afraid that it would ruin our relationship, but having her tell me she is proud of me made me very happy.
Over the next few days, the rest of my interview segments appeared on the show and the following week Joanna's segments were shown. Soon we were getting calls from other networks to appear on other shows including Chelsea Lately, The Tonight Show Starring Jimmy Fallon, and Arsenio. Following the appearances, we were also featured in issues of Rolling Stone and Entertainment Weekly. In the magazines we shot a few photos as Tiffany and Joanna and gave interviews discussing our start, what it was like playing women, reactions from the public and our loved ones, and our future plans. Eventually, we were each given our own regular segments. I became a regular guest panelist on Chelsea Lately and Joanna became a correspondent on Extra. For his role on Extra, Jonas played Joanna as less of a character and more as a real woman to fit the style of the other female correspondents on the show.
On the night of the Webbys, we were both unsure whether to attend the ceremony as ourselves or in character. While our fans knew us as our characters, we also wanted to make sure they knew that Tiffany and Joanna were only characters and not who we really were. In the end, Jonas and I arrived at the ceremony in tuxedos with our girlfriends and my mother by our side. We ended up winning that night and when we went on stage we thanked everyone for all of their support. As I looked at the crowd, I felt a sense of accomplishment in knowing that we had finally found success. It may have been by dressing as women, but we were successful nonetheless.
Now that we both had jobs on television, we found it difficult to maintain a regular presence on the website. Although Jonas and I had made it in the industry, we didn't want to leave our friends behind. Without Doug and Eddie we would have never gotten where we were and we couldn't abandon them. Also, shortly after I began as a regular on Chelsea Lately, Gwen told me she was pregnant. She had recently gotten a supporting role on a sitcom and we were both torn as to what we should do. While it had been both our lifelong dreams to make it in the industry, we also both dreamed to have a family together. Gwen's sitcom was nearly done shooting for the season and she agreed to take a break from acting until the baby was born. I, in turn, cut down my appearances on Chelsea Lately to spend more time with Gwen in the months leading up to the birth of our baby.
Tim gets his first national TV exposure when he and Jonas are invited to do a few correspondent segments as Tiffany and Joanna on Jimmy Kimmel Live! The segments soon lead to them appearing on more TV shows and eventually getting jobs on Extra and Chelsea Lately. In this chapter, they also win a Webby and Tim learns he and his now fiancee Gwen are having a baby.