Ross was 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 the 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 then made host of Radio WWF, alongside Monsoon (Gorilla Monsoon), which lasted under a year. In this role, Ross was joined by co-hosts such as Johnny Polo, and talked to various WWF wrestlers and fans. Ross and Monsoon called SummerSlam and Survivor Series at the end of 1993 and the Royal Rumble for Radio WWF.
Ross was fired by Vince McMahon on February 11, 1994.
After a few weeks of Gorilla Monsoon on play-by-play, the WWF rehired Ross to fill in for McMahon alongside Randy Savage throughout that summer. When McMahon was acquitted, Ross was let go by the WWF again. The WWF rehired him in early 1995 in time for WrestleMania XI. Relocated to the syndicated WWF programming for the majority of the next two years, 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 Diesel and Razor Ramon leaving the WWF, Ross began to proclaim on television that he was still in touch with "Diesel" and "Razor Ramon" 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, claiming that while working in the WWF "front office" he had been the man responsible for so many people leaving the company as part of his "revenge" against the WWF for how they treated him in the past. 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, due to another attack of Bell's palsy which came the day after the death of his mother. On March 1, 1999, he returned to Raw Is War as part of a storyline alleging that Vince fired him because of his condition, but that he would not go down quietly and enlisted the services of "Dr. Death" Steve Williams as his personal "enforcer". The storyline went as far as to have Jim Ross set up his own announce table in front of the official announce table labeled "JR Is RAW." Shortly after that, Jim Ross confronted his replacement, Michael Cole, in the ring. After minutes of Cole trying to convince that he was not trying to steal Ross' job, Ross kicked Cole in the crotch and left the ring. 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 as WWE became the sole major wrestling promotion in North America. 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. Also during this time, Ross served as an Executive Vice President of Talent Relations for the WWF/WWE, a codified extension of his long-time backstage role as a key individual in charge of hiring new talent. By 2005, Ross had stepped down from his executive and management roles.
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. Doctors had discovered a serious issue with Ross's colon, and his storyline termination provided an explanation for his absence. While recovering from his colon surgery, Joey Styles called the weekly Raw. After recovering, Ross helped produce the Raw announcers from backstage, and was brought back for Saturday Night's Main Event in 2006, then the Raw-brand matches at WrestleMania 22, 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".
Ross' contract with WWE expired in October 2006. At that point, neither side had signed a new contract and instead worked week to week under the terms of the expired contract. In November 2006, Jim Ross stated on JR's BBQ that he had signed a new one-year contract with WWE and would continue to work year-to-year.
On March 31, 2007, Ross was inducted into the WWE Hall of Fame 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 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, Ross announced on his WWE Universe blog that with the departure of Tazz from World Wrestling Entertainment, he 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 broadcasting as a full-time announcer for WWE.
Ross missed the SmackDown tapings on October 13, 2009, as he asked for a day off due to an anniversary. Seven days later, on October 20, Ross suffered his third Bell's palsy episode en route to Columbia, South Carolina for a SmackDown taping. After initially planning on working the tapings and reuniting with Lawler, Ross instead flew back to Oklahoma, missing the show—Lawler and Cole commentated SmackDown—and leaving his plans for Bragging Rights in the air. On October 21, 2009, Jim Ross announced that he would not be commentating the WWE Bragging Rights pay-per-view, but Grisham mentioned that SmackDown would give Ross the Bragging Rights trophy as a "get well" gift.
On the November 15, 2010, live three hour special Old School Raw from the Giant Center in Hershey, Pennsylvania, Ross made a guest appearance on commentary with Jerry Lawler and Michael Cole, calling a match between Daniel Bryan and Jack Swagger. This was Ross' first television appearance in over one year. Cole insulted Ross throughout the match, which resulted in Ross hitting Cole over the head with his hat after the match had finished.
On the March 14, 2011 episode of Raw from the Scottrade Center in St. Louis, Missouri, Ross made another guest appearance, trying to talk some sense into Cole, who over the last few months began a feud with Jerry 'The King' Lawler. Ross would get insulted some more by Cole, which made Ross challenge Cole to a fight, only for Jack Swagger to come out and attack both Lawler and Ross.
Ross came back at WrestleMania XXVII to call the final four matches on the card, including the Cole/Lawler match. He also made an appearance on the following night's Raw program, alongside Jerry Lawler, whom he called the last three matches of WrestleMania with the night previous. He left Raw later that night after Cole squirted him with his barbecue sauce, which legitimately got in his eye and caused Ross to need one of his eyes flushed by the Medical Trainers backstage.
Since returning to the announce table the night after WrestleMania XXVII on Raw, Ross once again became an unofficial Raw commentator, reuniting with Jerry Lawler, then the next week, managing Lawler in his re-rematch with Jack Swagger. Following the match, which King won, thus gaining the right to pick the type of match and stipulation for a rematch between him and Michael Cole at Extreme Rules, he chose a tag team match, where he and JR would face Michael Cole and the man Cole pushed, poked and slapped after losing to King that night, Jack Swagger. JR then called the rest of the show with Lawler and Josh Mathews, serving in the role he portrayed when he was last a full-time commentator on WWE programming providing a mix of both color and play-by-play commentary.
On the April 18 episode of Raw from the United Kingdom, during Michael Cole's knighting ceremony, Ross was forced to kiss Cole's fungus-infected foot and miss the remaining two matches that night after also, once again, receiving an Ankle lock from Jack Swagger.
The next week on Raw, the 2011 WWE Draft version of the show, Ross faced Michael Cole in the only match of the night not worth a Draft pick for a Brand. The match was almost five minutes long, most of which was Cole taunting Ross, most notably with the Kamala belly pat and wearing JR's hat, only to take it off and step on it in the ring and kick it out of the ring. Ross legitimately broke his hand, as well as cut himself on his right knuckle and bust Cole's lip, causing Cole to bleed from inside his mouth. Ross won the match by disqualification when Swagger came in and attacked him. Lawler, who was at ringside with Ross to counteract Swagger's being at ringside for Cole, got in after being attacked by Swagger on the outside of the ring earlier and took out Swagger after Cole whipped Ross' back with his belt, which Swagger took off of him before putting him in the Ankle Lock. Lawler whipped Cole on his behind with the same belt, which prompted the Anonymous Raw General Manager to make the Tag Match between the four at that Sunday's Extreme Rules a Country Whippin' Match, the second of Ross' career. Cole ran off holding his behind as JR showed Lawler his busted knuckle, as well as the blood on his right cheek. Lawler & Ross ended up losing at Extreme Rules, when Cole pinned Ross with a roll-up.
At Over the Limit on May 22, Ross showed up to gain revenge on Cole for squirting him with his own barbecue sauce a couple of months before on Raw. JR brought his own bottle of sauce to the ring with him and proceeded to pour it all out over Cole's face, hair and clothes. Things only got worse from there for Cole, as Bret Hart made a surprise appearance and locked in the Sharpshooter, while Lawler made Cole kiss his foot. After that, he joined the announcer's table alongside Josh Mathews and Booker T to call the "I Quit Match" of John Cena and The Miz.
On July 25, 2011, the new COO of WWE, Triple H re-hired Ross to a full time commentating position on Monday Night Raw to reform the partnership between himself and Jerry Lawler (alongside Michael Cole). On September 19, Jim Ross interviewed Mark Henry on winning the World Heavyweight Championship from Randy Orton at Night of Champions, but only to be attacked by him. Jerry Lawler tried to stop him but he received a World's Strongest Slam. Ross and Lawler were replaced by Josh Mathews for the rest of the night.
On the October 10 episode of Raw, Ross was fired by the new Raw Interim General Manager, John Laurinaitis, for walking out on Triple H the week before. Ross later revealed that he was given no prior notification that he was to be publicly fired like he was. On the October 17 episode of Raw, Ross returned in a tag team match with John Cena in a win over Michael Cole and Alberto Del Rio. A week later, Cole would challenge Ross to a "Michael Cole Challenge" match, where if Cole would lose, he would quit. Despite this, on the Halloween special episode of Raw, Ross "no-showed" the "Michael Cole Challenge" due to inflammatory bowel disease. The Michael Cole challenge was rescheduled for the following week, but again was cancelled. The challenge was yet again scheduled for the November 14 episode, and was slated to kick off that night's episode. In the episode Ross won two of the three challenges which were arm wrestling and dancing but lost the final challenge which was who weighed less. Subsequently, he was "fired" again.
On the 12/12/2011 edition of RAW at the Slammy Awards, JR won the slammy award for "tell me I just did not see that". He then got in a rap battle against Michael Cole which JR won. He then celebrated by doing the Spinnaroonie.
On April 1, 2012, at WrestleMania XXVIII, Ross, sporting a new beard, returned to call the 'End of an Era' Hell in a Cell match between Triple H and The Undertaker per Undertaker's request behind the scenes. It was also noted that he ended his long time feud with Michael Cole as the 2 shook hands healing any old wounds they had between them.
On the September 17th and October 8th episodes of Raw, Jim Ross joined Michael Cole & JBL at commentary filling in for Jerry Lawler.
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, 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 local wrestling legends Bill Watts and Danny Hodge after Raw went off the air.
On December 17, 2012, during the WWE Raw, Jim Ross appeared alongside Gene Okerlund and Ricky The Dragon Steamboat to announce the winner of the Slammy Award for Match of the Year. Ross also returned 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. Michael Cole allowed Ross to replace him to call the match alongside JBL and Jerry Lawler.
On March 1, 2013, Jim Ross made a return to Friday Night SmackDown to interview his long-time friend Jack Swagger, and Swagger's advocate, Zeb Colter. Swagger began provoking Ross, saying he wasn't a "real American". Alberto Del Rio ran down the ramp and into the ring and gave Jim Ross his cowboy hat back, which Jack Swagger originally knocked off. On April 7, Jim Ross appeared to host the WrestleMania 29 pre-show and post show alongside Dusty Rhodes, Kofi Kingston and Scott Stanford.
He announced his retirement from WWE on September 11, 2013.