Britney Spears And Don Philip: 'X Factor' Judge Boots Singer Who She Recorded With In 1999 (VIDEOS)

The second season of Simon Cowell's "The X Factor" kicked off Wednesday night and new judge Britney Spears was put to the test when judging "X Factor" contest Don Philip, who she recorded a song with back in 1999.

It was undoubtedly one of the biggest moments of the "X Factor" premiere and the "Womanizer" singer's biggest challenge as a newbie judge.

Philip, a now a 32-year-old vocal coach who is hard on his luck, was Spears' duet partner on the song "I Will Still Love You," which was featured on her 1999 smash-hit debut album, ...Baby One More Time. When he took the stage, Philip was an emotional wreck.

"I've been really working hard. I've been doing more writing and producing, trying to really find my sound," Phillip said to the "X Factor" cameras before the audition. "I've had a lot of 'maybes' and a ton of 'almosts.' This one thing. I think this is my final chance. There's no more after this. This has to be it for me. I've tried every other way."

When he finally stepped in front of the judges, the pop star recognized him immediately and she was shocked. "Oh my gosh," said Britney. "I know him."

But when Cowell asked Philip what he had done in the last 10 years, the vocal coach broke down in tears and discussed his professional letdowns. Unfortunately, the letdowns continued when Philip gave a dismal performance of Beyonce's "Halo" and the tense judges, including Spears, were forced to tell him "no."

“You don’t have a good singing voice, honestly,” Cowell told Philip.

Spears tried to let him down easy: “I feel like through the years maybe you’ve gone through a lot of hardships and battles, but your voice really isn’t up to the bar of the standards of 'The X Factor' and what we want.”

Fox chose not to air the portion of the segment when Philip revealed that he is gay on stage, Celebuzz reported.

“To be honest with you, when I saw Britney I cried a little,” he told Celebuzz in an exclusive interview. ”I never thought I would see her again. I didn’t know I would even come back as a singer, because I was so consumed in myself and figuring out my life and my sexuality.” reported Carla Hay, who attended the Oakland auditions, said that Philip received a negative reception on "The X Factor" not becausehe is gay, but because he made the environment palpably tense.

"My eyewitness account is that Philip made a complete fool out of himself, not because he announced that he was gay but because he spent several minutes rambling and acting like a nutcase before he actually sang," wrote Hay. "Not only did he get booed by the audience, but he also got a less-than-warm reception from judges Spears, Simon Cowell, L.A. Reid and Demi Lovato, who all voted 'no' after his audition."

Philip took to his Facebook to respond:

Now this is what i have to say about Britney Spears and I now know this to be true..--Britney didn't care about me being gay---she is the least judgmental person I know-she accepts folks that accept and embrace themselves and their differences!! i will still love you britney for always.. and now to focus on the job at hand to build that house in Manila for Brother Joe Dean..and the CHILDREN...

Listen to Don Philip's duet with Britney Spears on "I Will Still Love You" below.

The X Factor