After Arrieta graduated from high school, he enrolled in the "Universidad del Sagrado Corazon" (University of the Sacred Heart) of San Juan, where he earned a Bachelors Degree in "Radio and Television Production". There, he joined Phi Sigma Alpha Fraternity.
On one occasion, Arrieta and some friends visited the café theater "El Punto del Coqui" located in "Old San Juan". He sat down and played the piano while doing imitations. The owner of the club was impressed and asked Arrieta to prepare an act for his club. Arrieta prepared an act called "Black and White" which was a success and he was soon traveling around the island with his "show".
In 1991, Arrieta went to Mexico where he participated in the play "Mama ama el Rock" (Mother loves Rock) with Mexican stars Angelica María and Angelica Vale. That year, he also co-hosted the TV show "Lente Loco" ("Crazy Lens"), a Candid Camera-style show with the Cuban model Odalys Garcia.
Later in the nineties, he got his own show "Que Vacilón" aired in prime time through WAPA. In this comedy show of sketches and stand-ups, he brought to life, along with other local talents, a bunch of peculiar characters who gained immense popularity in the Puerto Rican pop culture, like the clown Trompetilla, a grumpy clown with a kind of fraudulent circus; and Andresito a kind of Dennis the Menace little boy. Many consider this period to be the peak of his career.
Arrieta had his own weekly TV show in Puerto Rico called "El Show de Raymond". Which was transmitted through Televicentro and Wapa TV. In 2007 he switched to Telemundo and WKAQ-TV, where he stars in his own daytime daily show, "Día a Día con Raymond y Dagmar". Puerto Rican comedian, Jose Miguel Agrelot once said, that Raymond Arrieta was the greatest comedian of the "new" generation.
|Florencio Melón Pujals||Charlie Too Much parody|
|Crispina||Cristina Saralegui parody|
|María Plinia Palerm Carbetó||aka. Plinia|
|Pedro Queselló||Pedro Rosselló parody|
|Wally||Walter Mercado parody|
|Chef Piñón||Chef Piñero parody|
|El Maricuazo||Jesús Omar Rivera "El Boricuazo" parody|
|Cayayo Culombo||African character|
|1991-1996||Lente Loco||Host||TV Show|
|1997||Quiero ser Estrella||Host||TV Show|
|1997 - 2007||El Show de Raymond||Host||TV Show|
|2004||El Sueño del Regreso||Flight attendant||Movie|