Boland played Lancelot in the musical Camelot at El Camino College in 1986.[4] Theater critic Bill Dorsett wrote in the Daily Breeze, "Boland makes his first entrance and before he can say 'moi' he has the audience in his pocket."[4] He played the revolutionary Norman Cornell in the Neil Simon comedy The Star-Spangled Girl in a 1985 Chapel Theater run in Lomita, California.[5] The critic Dorsett said that "Boland plays Norman very low-key during the opening scenes, but quickly warms up to the level of the rest of the cast. Boland has some of the best comedy business in the show, and most of the time he handles himself very well on stage."[5] Boland assumed the role of F. Sherman in the Bill Manhoff comedy The Owl and the Pussycat in 1986 for Chapel Theater.[6]Daily Breeze reviewer James Bronson criticized his performance, writing, "Boland is low-key -- in fact, too low key -- through much of the play. And he doesn't show an inherent comedic sense, which keeps the play flat."[6] At the Lomita restaurant and nightclub Seymour Hamms in 1986, Boland acted as the baron Cletis T. Fullernoy in the James McLure play Lone Star.[7]Daily Breeze reviewer Bill Dorsett wrote that Boland "proves his versatility in the nerdy role" since within the last year, he "has given memorable performances in The Star Spangled Girl, Camelot and now Lone Star playing three very different characters expertly."[7]
At Seymour Hamms in 1987, Boland produced and staged the musical show "Be-Bop-A-Lula" that showcased music from the 1950s and 1960s.[8] Boland hosted a 2.5-hour musical show, "A Tribute to Neil Diamond", in 1988 at Seymour Hamms. Daily Breeze reviewer Shari Okamoto found that "Saturday's show wasn't perfect, but it was a flattering tribute to Diamond and rousing entertainment for people not familiar with his work."[9]
Boland performed for the Apollo Theater Chicago show "Al Anthony's Salute to the Superstars" in 1991. In a positive review, Chicago Tribune theater critic Richard Christiansen wrote that the show was "strictly phony, but at least the phoniness is genuine and unpretentious" and said of Boland's performance, "When Paul Boland, not even looking or particularly singing like Elvis Presley, comes on and does an amiably offhand, what-the-hell turn as The King, the mature ladies who chat and dance with him no doubt feel they are in the presence of a real rocker."[14] He performed at The Mirage on the Las Vegas Strip around 1992.[2]
He was the game showannouncer for the 1998 revival of Match Game.[15] Boland performed song impersonations at a Ray Charles concert in San Diego in 1999.[16]The San Diego Union-Tribune music critic Mikel Toombs had a negative review of Boland's work, writing, "Some of Boland's bits had an entertaining familiarity -- and some didn't, which is death to an impressionist -- but his lack of imagination showed why he's stuck on TV hosting a recycled game show ("The New Match Game")."[16]
Boland performed on the Cunard Line's cruise ship Queen Elizabeth 2 in 1999.[17] In a review of Boland's performance, The Gazette columnist Gus Schrader wrote, "We enjoyed Boland the most. He is a versatile young man you probably will be seeing on TV - or maybe already have. He rivaled impressionist Rich Little with his clever lines as he imitated famous people, mostly singers."[17] He filled in for announcer Rod Roddy on The Price Is Right in 2002 during Roddy's cancer operations.[18][19] After Roddy died, Boland auditioned to become announcer, but Rich Fields received the role.[20]George Hamilton called Boland "the very best there is" and Wayne Newton said he is "one of the greatest entertainers I know".[21]