A Meeting of Two Irresistible Performers
There are some television performances that feel less like formal productions and more like wonderfully spontaneous evenings shared with old friends. Dean Martin and Ann-Margret’s appearance on The Dean Martin Show in 1970 belongs firmly in that category. Their medley of “Hey, Good Lookin’,” “(Sittin’ on) The Dock of the Bay,” “That Old Feeling,” and “I Take a Lot of Pride in What I Am” brought together four very different songs and transformed them into one relaxed, playful, and surprisingly warm musical conversation.
Broadcast on February 26, 1970, the performance captured everything that made variety television so appealing during its golden era. There was no need for excessive production or elaborate staging. The charm came from the personalities, the arrangements, and the easy chemistry between two performers who understood how to entertain an audience without appearing to try too hard.
Dean Martin, already celebrated as a singer, actor, and television host, brought his familiar blend of cool confidence and understated humor. Ann-Margret, meanwhile, offered sparkle, energy, and a naturally expressive stage presence. Together, they created a contrast that made every change in musical mood feel fresh.
Opening with Hank Williams’ “Hey, Good Lookin’”
The medley begins with Hank Williams’ “Hey, Good Lookin’,” a song built around flirtation, optimism, and easy country swing. It is an ideal opening because it immediately establishes a lighthearted atmosphere. The tune is recognizable within seconds, yet Martin and Ann-Margret give it enough personality to make the performance feel like their own.
Martin’s delivery is characteristically relaxed. He never sounds as though he is forcing the rhythm or chasing the melody. Instead, he settles into the song with a conversational ease, allowing the humor and flirtatious spirit to come naturally. Ann-Margret responds with a brighter, more animated energy, giving the opening a playful back-and-forth quality.
The appeal of this section lies in its simplicity. Rather than treating the song as a museum piece from country music history, the performers make it feel immediate and alive. The arrangement leaves room for smiles, glances, and small gestures, reinforcing the impression that the two stars are enjoying the song as much as the audience is.
A Soulful Turn Toward “The Dock of the Bay”
The transition into Otis Redding’s “(Sittin’ on) The Dock of the Bay” provides one of the medley’s most interesting changes in direction. After the upbeat country charm of “Hey, Good Lookin’,” the performance moves into a more reflective and soulful space. It is an unexpected choice for Martin’s easygoing style, but that contrast is precisely what makes the moment memorable.
Martin does not attempt to imitate Redding’s unmistakable intensity. Instead, he approaches the song from his own musical world, emphasizing the quiet resignation and thoughtful mood hidden beneath the melody. His phrasing gives the number a gentle swing, creating a version that feels intimate rather than dramatic.
Ann-Margret adds a soft emotional color to the arrangement. Her presence helps broaden the song’s feeling without overwhelming its understated character. The result is not a competition between two vocalists, but a shared interpretation. Their voices seem to meet in the middle, balancing Martin’s laid-back delivery with Ann-Margret’s warmer, more expressive tone.
This section also demonstrates why medleys can be so effective in a television setting. In only a few minutes, the audience is taken from playful romance to quiet contemplation. The change keeps the performance moving while allowing both singers to reveal different sides of their personalities.
The Romantic Warmth of “That Old Feeling”
With “That Old Feeling,” the mood becomes more tender. The standard has long carried the atmosphere of rediscovered romance, and Martin’s vocal style is perfectly suited to its elegant nostalgia. He sings with the kind of effortless polish that made him one of the most recognizable crooners of his generation.
Ann-Margret’s contribution gives the song a sense of freshness. Her performance does not simply echo Martin’s approach; it adds a youthful emotional lift that complements his seasoned restraint. When the two voices come together, the song takes on the feeling of two people remembering a powerful connection that never completely disappeared.
The chemistry here is especially important. Neither performer oversings, and neither tries to dominate the spotlight. Instead, the arrangement allows the romantic character of the song to develop through restraint. A glance, a smile, or a slight change in phrasing can communicate as much as a large vocal flourish.
This is one of the quiet strengths of the entire medley. Martin and Ann-Margret understand that classic popular songs do not need to be dramatically reinvented to remain effective. Sometimes, the best approach is to respect the melody, trust the lyrics, and allow personality to do the rest.
Closing with Merle Haggard’s “I Take a Lot of Pride in What I Am”
The final selection, Merle Haggard’s “I Take a Lot of Pride in What I Am,” gives the medley a distinctly country-minded conclusion. The song’s message of self-respect, humility, and personal identity provides a meaningful contrast to the flirtation of the opening number and the romance of the middle section.
Martin brings a casual dignity to the performance. His voice suggests someone who has lived through enough to understand the value of the song’s message, yet he never turns the interpretation into a heavy-handed statement. Ann-Margret responds with sincerity and warmth, helping the finale feel celebratory without becoming overly sentimental.
Ending with this song was a smart choice. It leaves the audience with a sense of character rather than simply romance or nostalgia. The performance becomes a tribute to ordinary pride, hard-earned confidence, and the ability to remain true to oneself. Those themes were central to Haggard’s writing, and they translate naturally into the relaxed atmosphere of the television stage.
Why the Performance Still Works
More than five decades later, this medley remains enjoyable because it captures a style of entertainment that valued charm above spectacle. The Dean Martin Show was built around Martin’s easy rapport with guests, and this appearance shows how effectively that format could highlight musical chemistry.
Ann-Margret was an ideal partner. Her exuberance never clashes with Martin’s cool delivery; instead, it gives the performance movement and color. Martin’s calm presence, in turn, provides a steady center for her energy. The contrast creates a natural rhythm, much like a conversation in which both people know when to speak, when to listen, and when to let the other person shine.
The medley also reflects the wide musical landscape of the late 1960s and early 1970s. Country, pop, soul, and traditional standards could exist side by side, connected by strong melodies and charismatic performers. Rather than separating these genres, Martin and Ann-Margret move through them with confidence, showing how much common ground they share.
A Charming Time Capsule of Variety Television
Dean Martin and Ann-Margret’s 1970 medley is not remembered because it relies on technical excess or dramatic theatrics. Its appeal is more enduring than that. It offers four familiar songs, two magnetic performers, and an atmosphere of genuine enjoyment.
From the country sparkle of “Hey, Good Lookin’” to the soulful reflection of “The Dock of the Bay,” the romantic elegance of “That Old Feeling,” and the proud finish of “I Take a Lot of Pride in What I Am,” the performance travels through several emotional landscapes without ever losing its relaxed personality.
For viewers discovering the clip today, it serves as a delightful reminder of why Dean Martin remains such a beloved figure in American entertainment and why Ann-Margret continues to command attention whenever she appears. Their chemistry is warm, their choices are entertaining, and their confidence makes the entire medley feel effortless. It is a small but shining example of television magic—joyful, graceful, and still capable of making an audience smile.