In 1987, Ross joined World Championship Wrestling (WCW) and began doing color commentary alongside David Crockett and Tony Schiavone. With his new position, Ross became the head play-by-play man for WCW until 1993, when he was released.
Ross was then hired by the World Wrestling Federation and made his on-screen debut at WrestleMania IX. He took over for Gorilla Monsoon on WWF Wrestling Challenge the following weekend. Ross worked alongside Bobby Heenan on the show until Heenan left the WWF in December 1993. Ross was originally the main voice of the WWF's pay-per-view events when he was first brought in, calling both WrestleMania IX and King of the Ring with Heenan and Randy Savage in 1993. Vince McMahon took over his position at pay-per-views starting with SummerSlam 1993. Ross was fired on February 11, 1994.
After a few weeks of Gorilla Monsoon on play-by-play for Monday Night Raw, the WWF rehired Ross to fill in for Vince McMahon alongside Randy Savage throughout that summer. After McMahon returned, Ross was let go by the WWF. The WWF rehired him in December 1994. Ross rejoined the primary announce team in the summer of 1996. In September 1996, Ross turned heel in WWF storylines for the first time in his career. Following Scott Hall and Kevin Nash's departure from the WWF for World Championship Wrestling and their debut there as The Outsiders, Ross began to proclaim on television that he was still in touch with Razor Ramon and Diesel (Hall and Nash's WWF personas, respectively) and claimed that he would be bringing them back to the WWF soon. Other announcers were skeptical, and WWF President Gorilla Monsoon said that Hall and Nash were under contract with "another organization", and ordered Ross to cease and desist mentioning them on the air. On the September 23, 1996 episode of Monday Night Raw, Ross delivered a worked-shoot promo during which he ran down WWF Chairman Vince McMahon (outing him as chairman and not just a commentator for the first time in WWF storylines) and debuted his "new" Diesel and Razor. While he was kept on the air by McMahon, Ross portrayed himself to be bitter and spiteful, with repeated potshots at McMahon. However, the "New Diesel-New Razor" storyline was poorly received by fans, and Ross' heel turn was quickly dropped.
After this angle, Ross went on to host various WWF programs such as Superstars, Action Zone, Raw Is War, and Shotgun Saturday Night. At the end of 1998, Ross took a break from Raw Is War. On March 8, 1999, he returned to Raw is War as part of a storyline alleging that McMahon fired him, but that he would not go down quietly and enlisted the services of "Dr. Death" Steve Williams as his personal "enforcer". Ross confronted his replacement, Michael Cole, in the ring. Despite Cole's insistence that he was not trying to steal Ross' job, Ross kicked Cole in the crotch and attempted to return to the announce table, though Terry Taylor ended up commentating for the rest of the night. The narrative went as far as to have Ross set up his own announce table in front of the official announce table labeled "JR Is Raw". The storyline was soon dropped as the attempt to turn Ross heel failed (the fans ended up cheering Ross and booing Cole) and he took his seat back as "official" commentator of Raw is War starting with the main event of WrestleMania XV.
Ross was the "voice of Raw is War" throughout the Monday Night Wars alongside Jerry Lawler and cemented his legacy as one of the great wrestling commentators. After the WWE Brand Extension, Ross worked exclusively for the Raw brand, cutting down to doing play-by-play on Raw-only pay-per-views, while SmackDown!-only pay-per-views were announced by SmackDown!'s announce team.
For most of the next six years Ross was involved in very few storylines.
Still working as the voice of Raw, Ross was again "fired" (kayfabe) from his play-by-play job by Vince and Linda McMahon on October 10, 2005. While gone, Joey Styles called the weekly Raw broadcasts. Ross was brought back for Saturday Night's Main Event XXXII in 2006, then the Raw-brand matches at WrestleMania 22 and Backlash before taking back his play-by-play job on Raw on May 8, 2006, after Styles quit Raw in the storyline, declaring his hatred for "sports entertainment".
On March 31, 2007, Ross was inducted into the WWE Hall of Fame class of 2007 by Steve Austin.
On June 23, 2008 during the 2008 WWE Draft, Ross was drafted from Raw to the SmackDown brand while Michael Cole was drafted from SmackDown to Raw, trading positions as commentators on each brand. This ended Ross' position as Monday Night Raw's play-by-play commentator after a nearly 12-year run.
On the September 23, 2008 episode of ECW on Syfy, Ross made an appearance on the ECW brand filling in for a sick Todd Grisham alongside Matt Striker.
On April 8, 2009, It was announced that with the departure of Tazz from World Wrestling Entertainment, Ross would assume the role of SmackDown's color analyst, with ECW announcer Todd Grisham moving over to the brand as the play-by-play announcer. October 6, 2009 was his last broadcast as a full-time announcer for WWE.
On the November 15, 2010 Old School Raw special, Ross made a guest appearance on commentary with Jerry Lawler and Michael Cole, calling a match between Daniel Bryan and Jack Swagger. Cole insulted Ross throughout the match, which resulted in Ross hitting Cole over the head with his hat after the match had finished. Ross returned on March 14, 2011 to confront Cole, who had entered into a feud with Lawler. After being insulted by Cole, he challenged him to a match but was attacked by Swagger. Ross called the final four matches at WrestleMania XXVII, including the Cole versus Lawler match. On the post-WrestleMania Raw, Ross joined commentary, only to walk out later in the night after Cole squirted him with barbecue sauce. Ross and Lawler defeated Cole and Swagger on the April 11 and 25 episodes of Raw but were defeated by Cole and Swagger in a Country Whipping match at Extreme Rules. As Lawler's feud with Cole ended at Over the Limit, Ross showed up to gain revenge on Cole by squirting him with barbecue sauce.
On July 25, 2011, the new COO of WWE, Triple H re-hired Ross to a full-time commentating position on Raw. The new Raw Interim General Manager, John Laurinaitis, fired Ross on October 10 for walking out on Triple H a week earlier. Ross returned on October 17, joining John Cena to defeat Michael Cole and Alberto Del Rio in a tag match. A week later, Cole challenged Ross to a "Michael Cole Challenge", with Ross's job on the line. The challenge took place on November 14; Ross won two of the three challenges, the first being a dance contest, the second being a rap battle (during which Ross legitimately forgot his lines) but lost the final challenge, which was who weighed less. Even though he lost the contest, he called the opening match of the night after Michael Cole was attacked by CM Punk.
At WrestleMania XXVIII, he returned to call the 'End of an Era' Hell in a Cell match between Triple H and The Undertaker. Prior to the start of the match, Ross shook hands with Michael Cole, effectively healing any old wounds they had between them. Ross also made an appearance at Raw 1000, commentating the opening match. On June 20, 2012, Ross took over as a commentator on the revamped NXT alongside Byron Saxton and William Regal. Following Jerry Lawler's heart attack on September 10, 2012, Ross returned to Raw to work as an interim commentator while Lawler recovered. Ross was honored on the October 1 edition of Raw as it was dedicated JR Appreciation Night and was held in his hometown of Oklahoma City. While CM Punk interrupted the segment as it aired, Ross was acknowledged by Vince McMahon and Triple H as well as legends Bill Watts and Danny Hodge after Raw went off the air. Ross also served as presenter for the Match of the Year award at the 2012 Slammy Awards.
He returned to television on the 20th Anniversary edition of Raw on January 14, 2013, where he called the steel cage main event between John Cena and Dolph Ziggler. On March 1, 2013 he appeared on WWE SmackDown to interview Jack Swagger, and Swagger's new advocate, Zeb Colter.
On September 11, 2013, Ross was released from the WWE.
On April 2, 2017, at WrestleMania 33, Ross returned to WWE, providing commentary for the main event No Holds Barred match between The Undertaker and Roman Reigns. Shortly after the event, it was announced that Ross had signed a two-year deal with the company. During the summer, Ross would provide commentary, alongside Lita, for the Mae Young Classic. On the January 22, 2018, episode of Raw 25 Years, Ross would reunite with Jerry Lawler as part of the commentary team that was at the Manhattan Center. On April 8, 2018, at WrestleMania 34, Ross called the fifth annual André the Giant Memorial Battle Royal on the WrestleMania 34 pre-show, alongside Jerry Lawler and Byron Saxton. Ross's last televised appearance for WWE was part of the pre-show panel for the Greatest Royal Rumble on April 27, 2018.
Ross left the WWE on March 27, 2019, after electing not to renew his contract.