Hutsell was born in Maryville, Tennessee where she attended Heritage High School, near the foothills of the Great Smoky Mountains, and she later the University of Tennessee. She began her career performing improv comedy at the Annoyance Theater in Chicago and also starred in their production of The Real Live Brady Bunch in 1990. The comedic stage show consisted of eight actual episodes of the cult classic TV show The Brady Bunch, with Hutsell cast as Jan Brady. The company toured to New York City, where Hutsell was hired as a cast member for the seventeenth season of Saturday Night Live.

Hutsell was a featured player from 1991–1993, and a regular cast member in the 1993–1994 season. She would eventually reprise her Jan Brady portrayal on a series of Weekend Update appearances, making it Hutsell's most recognizable recurring character. Hutsell also played a sorority pledge named Di in a series of sketches about the sorority Delta Delta Delta, along with Siobhan Fallon and Beth Cahill. Her most notable impressions were of Tonya Harding and Tori Spelling, an Actress whom she resembled.

After her film Can't Stop Dancing (1999), Hutsell quit show Business to raise her daughter, Carly Rose.

Hutsell is currently returning from retirement. She appeared in He's Such a Girl, a 2008 comedy also starring Ed Begley Jr.

In May 2009 she appeared as a guest on "Best Dishes" with Paula Deen on the Food Network. She announced that she is making a comeback, focusing on writing.

She played the role of Carol in the 2011 comedy hit Bridesmaids.

In 2015, Hutsell attended the 40th anniversary special of Saturday Night Live.

In 2016, she appeared in the role of Kristen Rhydholm-Rhydholm in the Netflix original series Lady Dynamite.