Set<File> files = new HashSet<File>();
files.add( // selected first file from entity File )

Set<Music> musics = new HashSet<Music>();
musics.add( // selected first music from entity Music )

new Playout(1,'Title1', files, musics);

Set<File> files = new HashSet<File>();
files.add( // selected first file from entity File )

Set<Music> musics = new HashSet<Music>();
musics.add( // selected first music from entity Music )

new Playout(2, 'Title2', files, musics)

36750 ["http-bio-8080"-exec-9] WARN org.hibernate.util.JDBCExceptionReporter - SQL Error: -104, SQLState: 23505
36750 ["http-bio-8080"-exec-9] ERROR org.hibernate.util.JDBCExceptionReporter - integrity constraint violation: unique constraint or index violation; SYS_CT_10052 table: PLAYOUT_MUSIC
36750 ["http-bio-8080"-exec-9] ERROR org.hibernate.event.def.AbstractFlushingEventListener - Could not synchronize database state with session org.hibernate.exception.ConstraintViolationException: Could not execute JDBC batch update

SELECT * FROM File;
FILEID   FILENAME
1   file1
2   file2
3   file3
4   file4
5   file5

SELECT * FROM Music;
MUSICID   COMPOSER   MUSICTITLE   TIME
1   ComposerA   Title1      00:20:00
2   ComposerB   Title2      00:21:00
3   ComposerC   Title3      00:21:00
4   ComposerD   Title4      00:23:00
5   ComposerE   Title5      00:25:00

SELECT * FROM Playout;
PLAYOUTID   TIME      TITLE
1      2011-07-31   Title1

@Entity
@Table(name="PLAYOUT")
public class Playout implements Serializable {

   @Id
   @GeneratedValue
   @Column(name = "playoutId")
   private Long playoutId;
   private String title;
   private Set<File> versionFiles;
   private Set<Music> musics = new HashSet<Music>(0);

   public Playout() {}
   
   public Playout(String filetitle, Set<File> files, Set<Music> musics) {
      this.title = filetitle;
      this.versionFiles = files;
      this.musics = musics;
   }

   @Id
   @GeneratedValue
   @Column(name = "playoutId")
   public Long getPlayoutId() {
      return playoutId;
   }

   public void setPlayoutId(Long playoutId) {
      this.playoutId = playoutId;
   }

   public String getTitle() {
      return title;
   }

   public void setTitle(String title) {
      this.title = title;
   }

   @OneToMany
   @JoinTable(name = "PLAYOUT_FILES",
         joinColumns = { @JoinColumn (name = "playoutId")},
         inverseJoinColumns = { @JoinColumn (name = "fileId") }
   )
   public Set<File> getVersionFiles() {
      return versionFiles;
   }

   public void setVersionFiles(Set<File> versionFiles) {
      this.versionFiles = versionFiles;
   }

   @OneToMany
   @JoinTable(name = "PLAYOUT_MUSIC",
         joinColumns = { @JoinColumn (name = "playoutId") },
         inverseJoinColumns = { @JoinColumn ( name = "musicId") }
   )
   public Set<Music> getMusics() {
      return musics;
   }

   public void setMusics(Set<Music> musics) {
      this.musics = musics;
   }
}

@Entity
@Table(name="FILES")
public class File implements Serializable {

   private static final long serialVersionUID = 1L;

   @Id
   @GeneratedValue
   @Column(name = "fileId")
   private Long fileId;
   private String filename;

   public File() {
   }
   
   public File(String filename) {
      this.setFilename(filename);
   }

// setters and getters for fields: fileId, filename
}

@Entity
@Table(name="MUSIC")
public class Music implements Serializable {

   private static final long serialVersionUID = 1L;

   private Long musicId;
   private String musicTitle;
   private String composer;
   private String time;
   
   public Music() {   
   }
   
   public Music(String musicTitle, String composer, String time) {
      this.musicTitle = musicTitle;
      this.composer = composer;
      this.time = time;
   }

   @Id
   @GeneratedValue
   @Column(name = "musicId")
   public Long getMusicId() {
      return musicId;
   }

   public void setMusicId(Long musicId) {
      this.musicId = musicId;
   }

// setters and getters for fields: musicTitle, composer, time

}