Jonathan Scheinbart has assembled an annotated T’ai Chi song list

It’s reprinted here with his kind permission:

1.  "All of Me."  Singer: Willie Nelson.  Songwriters: Seymour Simons and Gerald Marks.  Link to lyrics and song:
The song reached number three on the country music charts. 
According to the Classics, T'ai Chi is rooted in the feet, transferred through the legs, directed by the center, and manifested in the fingertips.  The feet, legs, and center must act as one.  Indeed, the entire body is one unit.   Consequently, your opponent cannot take a part of you, but must instead take "all" of you. 
2.  "Both Sides, Now."  Singer/songwriter: Joni Mitchell.  Link to lyrics and song:
Rolling Stone ranked the song number 171 on its list of the 500 greatest songs of all time.
(a.)  The Classics ask us to be aware of differences.  Throughout our practice, we apply the principles of Yin and Yang, differentiating substantial from  insubstantial, primarily by shifting our weight from one leg to another.  
The song is also about differences.  It examines clouds, love, and life from "both sides."  Other lyrics also call to mind the Yin and Yang duality: "up and down"; "give and take"; "win and lose."    
(b.)  The songwriter regrets that, despite much study, she "really [doesn't] know clouds at all."  Some students may feel the same way.  Professor Cheng Man Ch'ing has important advice to offer:  "The secret is simply this: you must relax body and mind totally.  You must be prepared to accept defeat repeatedly and for a long period; you must 'invest in loss' ---otherwise you will never succeed."  
 3.  "Anticipation."  Singer/songwriter: Carly Simon. Link to lyrics: ; link to song: 
The song garnered Carly Simon a Grammy award nomination.
The song is about keeping our minds firmly grounded in the present moment ("stay[ing] right here"), not lost in speculation about what the future may hold.  When we are in a state of anticipation, focusing on the future (for example, "thinking about how right tonight might be"), we may be only dimly aware of what is actually taking place in the present.  Consequently, anticipation can "mak[e] [us] late" for (or miss entirely) events occurring in the present while we busily "keep [ourselves] waiting" for something else to happen in the future.   
Professor Cheng imparts a similar message.  He advises to  "seek the released mind," that is, one that is "easy," "calm but concentrated" on the postures, free of "anxiety, pride, ego," and other "extraneous thoughts and images."  "As you proceed through the postures, you must think totally on them, so totally, in fact, that the mind literally embraces the postures and vice versa." 
Sometimes a student, overlooking the Professor's teachings and anxious to advance to the next posture, begins a movement prematurely, omitting part of the transition.  The instructor may exclaim, "Don't anticipate!"   The song reminds us to avoid that error.     
4.  "It's Impossible."  Singer: Perry Como.  Adapted from the Spanish by Sid Wayne.  Link to lyrics and song:
"It's Impossible" was was one of Perry Como's most popular songs.
The song reminds us that the Form is not a possible thing. 
5.  "Let's Take the Long Way Around the World."  Singer: Ronnie Milsap.  Songwriters: Archie Jordan and Naomi Martin.
Link to lyrics and song:
The song reached number one on the country music charts. 
The song reminds us that when transitioning from the first shuttle to the second, and from the third shuttle to the fourth, we "take the long way around."