The 101 Cafe began its life as a small 20-seat diner in 1928, opened by the Ekegren family. It was just the small dining room where the counters are now. As today, the restaurant was noted for its breakfast, which is still served all day. The Cafe was named for the old highway which it fronted Highway 101. The Greyhound bus stopped right in front until the 1940's when a bus station was located downtown. The diner enjoyed the traffic generated by Highway 101, which was the main access from Los Angeles to San Diego until 1953 when Highway 101 was relocated to the present location of Interstate 5. This changed the nature of the business.

During this time a local businessman had the foresight to adapt to the change. Lucky Lackey, the businessman, added the overhang around the building as it now exists. He found a successful restaurateur in John "Bushie" Graham to operate the latest in eateries, a drive-in called "Grahams" and ran it quite successfully until the early 1970's. Graham also ran two other drive-ins in Oceanside, located at Seventh and Hill Streets and Clementine and Mission Avenue. Grahams' reputation as a hot spot for local teenagers spread far and wide. When the new drive-throughs like McDonald's began to rise to prominence, drive-ins no longer prospered. Graham adapted by selling to-go items and changed the format to a coffee shop. All along, the Cafe has been a favorite of locals and tourists looking for friendly service and great food. About 10 years later, a new owner changed the name to Randy's Coffee Shop.