Phil Crosby Jr. Reflects on Dean Martin and Family Memories

In a nostalgic twist, Phil Crosby Jr. recently shared a quirky story about his mother’s past relationship with Dean Martin. Back in the day, when drive-thrus were still a novelty, Martin famously damaged a vintage car while trying to grab a hamburger for Phil’s mother’s son.

Phil, speaking to Fox News Digital, revealed that his mother, Peggy Crosby, had a whirlwind romance with Martin after her marriage to Phil Sr., Bing Crosby’s son, fell apart. “I was almost Dean Martin’s son-in-law,” he remarked, adding how different life could have been had that relationship worked out.

Phil reminisced about his mother meeting the famous singer at a club where she was working, describing her as a “young, beautiful woman.” At the time, Martin was quite a bit older than Peggy, and he remembered him as very lively and engaging.

One of his unique memories involved peeking into his mother’s bedroom and finding Martin asking him to fetch a pack of cigarettes. “He used to call me ‘that girl,'” Phil recalled, sharing that whenever his mother met Martin later, he was still referred to as “the kid.” It was a bit odd, he admitted, but it stuck with him.

He recounted a specific incident that had been passed down through stories — when Martin tried to make a quick trip to McDonald’s but ended up wrecking his classic car in the process. Crosby chuckled at how his mother laughed while recounting the moment, especially when they reached the drive-thru. The staff looked horrified at the noise coming from the car, with Martin casually sitting there.

Despite the mayhem, Phil believed Martin didn’t mind the car damage too much. “He wasn’t materialistic, really,” he said. “He was just a genuinely sweet guy.” Those interactions might have been fleeting, but they left an impression on Phil, who wishes he could have more vivid memories of Martin.

Crosby also expressed admiration for his grandfather, Bing Crosby. He reflected on the importance of Christmas traditions in their family and noted that even though he never met Bing, the essence of those celebrations remained strong. “Christmas was a big deal, with family gatherings and all,” he mentioned.

As for the holiday season, Phil has plans to release two new singles. One of them is a cover of a lesser-known Bing Crosby song, “A Time to be Jolly,” which he described as fun and a bit silly. “It’s something different,” he mused, hoping audio lovers will enjoy it.