During his first year at University of Hawaiʻi, Kaleikini had a part-time job at the Waikiki Sands. Kinney became a mentor to Kaleikini, who also learned from entertainer Leinaala Ignacio. After six months, Kaleikini moved with Kinney to the
Royal Hawaiian Hotel,
Hilton Hawaiian Village Kaleikini's first major break was at the
Hilton Hawaiian Village, where he performed for seven years. In July 1961, a review in the
Honolulu Star-Bulletin called Kaleikini "a charming shaker" who "has the correct shakes as he shows his versatility in doing the Hawaiian and Tahitian hulas." Kaleikini continued the residency at the Kahala Hilton for 28 years. Kaleikini typically opened the show with a multi-lingual greeting, The show's success was often attributed to Kaleikini's warmth and ability to charm the audience. Over the years, the show became more international in flavor, in response to more diverse audiences from around the world. Over 10,000 performances later, on April 27, 1987, Kaleikini celebrated his 20th anniversary at the Hilton with a two-hour show. In 1988, Governor
John Waihee officially declared Danny Kaleikini as "Hawaii's Ambassador of Aloha". In 2022, the Kahala Hotel & Resort honored him by renaming its front drive to Danny Kaleikini Square.
Performances in Japan Over the course of his career, Kaleikini became a frequent visitor to Japan and learned to speak Japanese. His visit to the Expo, accompanied by the popular Hawaiian sumo wrestler
Jesse "Takamiyama" Kuhaulua, helped to raise his profile and led to subsequent engagements in Japan. including
Olivia Newton-John. Kaleikini sang "The Snows of Mauna Kea" by Jay Larrin, Japanese classic "Koko ni sachi ari", and Frank Sinatra's "
My Way", in a program that was broadcast nationwide in Japan on August 3, 1986, by
Nippon Television Network. His first show was attended by an estimated 400 people from Hawaii, In December 1988,
Harrah's Reno in Nevada featured "Danny Kaleikini's Hawaiian Christmas", a one-week engagement at the Headliner Room. ==Radio, television, and film==