‘Roseanne’: 8 of Most Surprising Celebrity Guest Appearances

When Roseanne premiered in October 1988, the series was seen as a game-changing depiction of a working family in Middle America. As the series went on though, it attracted plenty of surprising guest stars who added some Hollywood glitz. Some of these stars were already icons by the time they arrived in Lanford, Illinois, while others were just on the cusp of fame. 

The list of surprising guest stars does not include arguably the biggest star to ever appear in the series: George Clooney. That’s because Clooney was an integral part of the show’s first season. He played Booker Brooks, the first foreman at Wellman who dated Laurie Metcalf’s Jackie. Clooney starred in 11 episodes during that first season, including the very first episode, “Life and Stuff.” He returned only one more time, appearing in the Season 4 episode “Trick Me Up, Trick Me Down,” which aired in 1991. Clooney would go on to star in Bodies of Evidence and Sisters, but it was not until 1994 that he scored his breakthrough role as Doug Ross on ER. And the rest is Hollywood history.

Today, The Conners has continued Roseanne‘s track record of bringing in big stars. The spinoff series is streaming on Hulu, but you have to turn to Peacock to check out Roseanne as of this writing. Scroll on to check out some of the most surprising stars who appeared on Roseanne.

Leonardo DiCaprio

As Entertainment Weekly points out, Leonardo DiCaprio made a pre-fame appearance in season three as a student in Darlene’s (Sara Gilbert) home-ec class. It was a non-speaking part, so you cannot be blamed for missing him. DiCaprio would later star in Growing Pains before landing his breakthrough film role in What’s Eating Gilbert Grape (1993). By the end of the ’90s, he was one of the biggest stars on the planet thanks to Titanic (1997).

Tobey Maguire

Tobey Maguire’s appearance on Roseanne came in 1991, during the same season as his friend DiCaprio’s. He had a couple of lines as Barry, a boy Darlene had a crush on, in the episode “Valentine’s Day.” In 2002, Maguire would find international stardom as Spider-Man in Sam Raimi’s trilogy.

Eric Dane

Long before Eric Dane was McSteamy on Grey’s Anatomy, he played a bellhop in the 1996 episode “Disney World War II.” In the season eight episode, he helped the Conners get settled into their hotel room. Dane later starred in Charmed, X-Men: The Last Stand, Burlesque, Euphoria, and The Last Ship.

Alyson Hannigan

Long before that one time at band camp, Alyson Hannigan appeared in the 1990 episode, “Like, a New Job” in season three. She played one of Becky’s (Lecy Goranson) friends who go to the diner where Roseanne got a job. Those who know Hannigan’s work from How I Met Your Mother and American Pie (1999) might be surprised to know that she started her career in the late ’80s. She starred in a short-lived 1989-1990 sitcom called Free Spirit.

Joseph Gordon-Levitt

A few years before Third Rock from the Sun, Joseph Gordon-Levitt appeared in four Roseanne episodes, from 1993 to 1995. He played George, one of D.J.’s friends. After Third Rock ended, Gordon-Levitt would find roles in (500) Days of Summer (2009), Inception (2010), The Dark Knight Rises (2012), and Snowden (2016).

Ellen DeGeneres

In season seven, Ellen DeGeneres stopped by to play Dr. Whitman, a marriage counselor Jackie (Laurie Metcalf) forced Fred (Michael O’Keefe) to see. At the time, DeGeneres was already starring in her sitcom, Ellen. After Ellen ended, DeGeneres reinvented herself as a daytime talk show host with The Ellen DeGeneres Show. The show ended in May 2022 after 19 seasons.

Neil Patrick Harris

Neil Patrick Harris certainly was no unknown star even when he appeared on Roseanne in 1992. By that point, Doogie Howser, M.D. had already been on for a couple of years. He played Dr. Doogie Howser in the episode “Less is More” in Season 4. Today, Harris is a four-time Golden Globe nominee and a five-time Emmy winner. He recently starred on Netflix’s A Series of Unfortunate Events.

Bruce Willis

At the very end of the Season 1 episode “Dear Mom and Dad,” which aired in April 1989, Bruce Willis made an uncredited cameo, slinking into Roseanne’s bed in place of John Goodman! At the time, Willis was best known on TV for Moonlighting, but he also made Die Hard the year before.