Tom realize his dream of being in a band the Metro, a club in Chicago. In 1997, the Plain White T's formed. The original members were Tom Higgenson, Dave Tirio, Steve Mast, and Ken Fletcher. They self-realeased an album, Come On Over, in 2001.
In the middle of making that album, Tom was in a car accident, where he ruptured a kidney, lacerated a lung, and broke three vertebrae. He was helping his friend move to college in 1999 when somebody cut him off and had had to swerve the van, flipping over, and sending Tom flying out the window into the grassy midsection on the highway. He had a brace on for 3 months and had to learn to walk again. It was a life-changing experience for him. Since that accident, his songs have become more personal. In 2002, the band released another album with Fearless Records, Stop.
The band then went through some line-up changes. Tom remained the lead singer, but Dave moved from drums to the lead guitarist, De'Mar Hamilton taking over the drums, and they were joined by Tim Lopez, the other guitarist and back-up vocals. The final member was Mike Retondo, the bassist and back-up vocals. In 2005, the band released another album with Fearless, All That We Needed.
All that we needed includes the famous acoustic "Hey There Delilah". 2007's "Hey There Delilah" was the single that exposed the band to the world. Light, sentimental and catchy, the song became a staple of FM radio and eventually sold over four million digital copies.
The next year, the Plain White T's coupled with another record company, Hollywood Records. That fall, they released Every Second Counts, and later on Big Bad World which was a departure for the band as the whole album was made entirely with instruments and methods that could have been found in the 1970's.
Tom appeared in the ABC Family show Greek, along with the other band members. The group performed as aband in several episodes of the show, and the song Our Time Now was used for commercials. Tom and Dave appeared as college students in one episode, only Dave had speaking lines however.